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Chemical Structure| 1722-10-7 Chemical Structure| 1722-10-7
Chemical Structure| 1722-10-7

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CAS No.: 1722-10-7

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Synonyms: 3-Methoxy-6-chloropyridazine

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Product Details of 3-Chloro-6-methoxypyridazine

CAS No. :1722-10-7
Formula : C5H5ClN2O
M.W : 144.56
SMILES Code : COC1=NN=C(Cl)C=C1
Synonyms :
3-Methoxy-6-chloropyridazine
MDL No. :MFCD00006467
InChI Key :XBJLKXOOHLLTPG-UHFFFAOYSA-N
Pubchem ID :74403

Safety of 3-Chloro-6-methoxypyridazine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3-Chloro-6-methoxypyridazine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1722-10-7 ]

[ 1722-10-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1722-10-7 ]
  • [ 13211-32-0 ]
  • [ 1591827-18-7 ]
YieldReaction ConditionsOperation in experiment
With silver nitrate; In water; trifluoroacetic acid; Step 1: 4-(tert-butoxymethyl)-6-chloro-3-methoxypyridazine To a mixture of tert-butoxy-acetic acid (5.7 g, 43 mmol) in TFA/water (20 mol percent, 48 mL) were added 3-chloro-6-methoxypyridazine (3.8 g, 26 mmol) and AgNO3 (0.42 g, 2.4 mmol). The mixture was heated to 70° C., then a solution of (NH4)2S2O8 (10.6 g, 46 mmol) in water (8 mL) was added dropwise. After addition, the mixture was stirred at 70-80° C. for 30 min. After cooling to r.t, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether: ethyl acetate (6:1) as eluent) to afford a mixture containing 4-(tert-butoxymethyl)-6-chloro-3-methoxypyridazine and 20-30percent 4-(tert-butoxymethyl)-3-chloro-6-methoxypyridazine (1.5 g).
  • 2
  • [ 67-56-1 ]
  • [ 1722-10-7 ]
  • [ 201230-82-2 ]
  • [ 13211-32-0 ]
  • [ 1591827-20-1 ]
  • [ 1591827-21-2 ]
YieldReaction ConditionsOperation in experiment
0.36 g; 0.1 g To a mixture of tert-butoxy-acetic acid (5.7 g, 43 mmol) in TFA/ water (20 molpercent, 48 mL) were added 3-chloro-6-methoxypyridazine (3.8 g, 26 mmol) and AgN03 (0.42 g, 2.4 mmol). The mixture was heated to 70 C, then a solution of (NH4)2S208 (10.6 g, 46 mmol) in water (8 mL) was added dropwise. After addition, the mixture was stirred at 70-80 C for 30 min. After cooling to r.t, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether: ethyl acetate (6: 1) as eluent) to afford a mixture containing 4-(tert-butoxymethyl)-6-chloro-3-methoxypyridazine and 20-30percent 4-(tert-butoxymethyl)- 3-chloro-6-methoxypyridazine (1.5 g). A mixture of 4-(tert-butoxymethyl)-6-chloro-3-methoxypyridazine containing 20- 30percent 4-(tert-butoxymethyl)-3-chloro-6-methoxypyridazine (1.3 g, 5.6 mmol), ethyl acetate (1 mL, 7.2 mmol) and Pd(dppf)Cl2 (130 mg) in MeOH (100 mL) was heated to 70 C with stirring under CO (50 psi) for 10 hr. After cooling, the mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate (3: 1) as eluent to afford methyl-5-(tert-butoxymethyl)-6-methoxypyridazine-3- carboxylate (0.36 g) and methyl 4-(tert-butoxymethyl)-6-methoxy pyridazine-3- carboxy late (0.1 g). MS (ESI) m/z 255 (M+H)+ Methyl 4-(tert-butoxymethyl)-6-methoxypyridazine-3 -carboxylate 1H NMR (CDCls, 400 MHz): delta 8.22 (s, 1H), 4.40 (s, 2H), 4.22 (s, 3H), 4.02 (s, 3H), 1.29 (s, 9H). Methyl 5 -(tert-butoxymethyl)-6-methoxypyridazine-3 -carboxylate 1H NMR (CDC13, 400 MHz): delta 7.40 (s, 1H), 4.77 (s, 2H), 4.20 (s, 3H), 4.00 (s, 3H), 1.29 (s, 9H).
  • 3
  • [ 1722-10-7 ]
  • [ 13211-32-0 ]
  • [ 1591827-18-7 ]
  • [ 1591827-19-8 ]
YieldReaction ConditionsOperation in experiment
With ammonium persulfate; silver nitrate; In water; at 70 - 80℃; for 0.5h; To a mixture of tert-butoxy-acetic acid (5.7 g, 43 mmol) in TFA/ water (20 molpercent, 48 mL) were added 3-chloro-6-methoxypyridazine (3.8 g, 26 mmol) and AgN03 (0.42 g, 2.4 mmol). The mixture was heated to 70 C, then a solution of (NH4)2S208 (10.6 g, 46 mmol) in water (8 mL) was added dropwise. After addition, the mixture was stirred at 70-80 C for 30 min. After cooling to r.t, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether: ethyl acetate (6: 1) as eluent) to afford a mixture containing 4-(tert-butoxymethyl)-6-chloro-3-methoxypyridazine and 20-30percent 4-(tert-butoxymethyl)- 3-chloro-6-methoxypyridazine (1.5 g).
 

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