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CAS No. : | 1074-86-8 | MDL No. : | MFCD01632221 |
Formula : | C9H7NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JFDDFGLNZWNJTK-UHFFFAOYSA-N |
M.W : | 145.16 | Pubchem ID : | 333703 |
Synonyms : |
4-formyl Indole;NSC 337264
|
Chemical Name : | 1H-Indole-4-carbaldehyde |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H317-H319 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium borohydrid; methylamine; In methanol; water; | Step C: To a solution of aldehyde product from Step B (2.0 g, 14 mmol) in methanol (100 mL), 40% methylamine in water (2.27 mL, 27.6 mmol) was added at room temperature over a period of 10 min. The mixture was stirred at room temperature under nitrogen overnight and then was cooled down to 0 C. Sodium borohydride (1.05 g, 27.6 mmol) was added. The reaction mixture was slowly warmed to room temperature for 2 h. Most of methanol was removed in vacuo, and the residue was diluted with water and extracted (3*) with ether. The combined organic layers were extracted with 2 N HCl (100 mL). The HCl layer was made basic (pH~11) with 2 N NaOH and extracted (3*) with methylene chloride. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give crude 4-(aminomethyl)-indole as a white powder (1.95 g, 88%): 1H NMR (300 MHz, CDCl3) delta 8.29 (s, br, 1H), 7.31 (d, J=8.0 Hz, 1H), 7.22 (t, J=2.7 Hz, 1H), 7.16 (t, J=8.0, 7.3 Hz, 1H), 7.08 (d, J=7.3 Hz, 1H), 6.64 (t, J=2.0 Hz, 1H), 4.06 (s, 2H), 2.51 (s, 3H); CI MS m/z=160 [C10H12N2+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium acetate; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 100℃; for 1 - 2h; | Example 109[0407] Preparation of 2-Amino-4-(lH-indol-4-yl)-5-oxo-7-(2,4,6-trimethyI-phenyl)- l,5,7,8-tetrahydro-4H-pyrano[4,3-b]pyridine-3-carboxylic acid ethyl ester. <n="150"/>[0408] Synthesis of 2-Amino-4-(lH-indol-4-yl)-5-oxo-7-(2,4,6-trimethyl-phenyI)- l,5,7,8-tetrahydro-4H-pyrano[4,3-b]pyridine-3-carboxylic acid ethyl ester (13oo): Ethyl amidinoacetate acetic acid salt is added to a 25-mL flask followed by lactone (1 equiv) and indole-4-carboxaldehyde (1 equiv). l-Butyl-3-methylimidazolium tetrafluoroborate (approx 2-3 drops/mmol of substrate) is added and the reaction mixture stirred at 100 0C for 1-2 hours. After completion (determined by LCMS), the reaction slurry is diluted with EtOAc and saturated NaHCO3. The organic layer is collected and the aqueous layer further extracted with 3 x EtOAc. The product is purified in 25-80% EtOAc in hexanes. MS (ES) M+H expect 472.2, found 472.2. |
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