ChemicalBook CAS DataBase List 7-CHLORO-1-HYDROXYISOQUINOLINE

7-CHLORO-1-HYDROXYISOQUINOLINE synthesis

8synthesis methods

Product Name:7-CHLORO-1-HYDROXYISOQUINOLINE
CAS Number:24188-74-7
Molecular formula:C9H6ClNO
Molecular Weight:179.6

1615-02-7
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$7.00/5g

26386-88-9
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$10.00/5g

24188-74-7
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$43.00/100mg

Yield: 53%

Reaction Conditions:

Stage #1:3-(4-chlorophenyl)prop-2-enoic acid;diphenyl phosphoryl azide with triethylamine in benzene for 2 h;
Stage #2: in Diphenylmethane at 90; for 3.5 h;Reflux;

Steps:

1001.1
Step 1To a solution of (is)-3-(4-chlorophenyl)acrylic acid (18.3 g, 0.1 mol) and Et3 (20.2 g, 0.2 mol) in benzene (100 mL) was added dropwise DPPA (27.5 g, 0.1 mol). After stirring for 2 h, the solution was concentrated and purified by chromatography (Biotage, mobile phase 20/80 EtOAc/hexanes) to give 16 g of an intermediate azide as a solid. This intermediate was dissolved in 100 mL of PI12CH2 and the resulting mixture was slowly heated to 90 °C over a 30 min time period. The reaction mixture was heated to reflux and maintained at this temperature for 3h. After cooling to RT, a solid precipitated which was collected by filtration and washed with toluene to provide 9.5 g of 7-chloroisoquinolin-l(2H)-one (53%). ^XH NMR (400 MHz, CD₃OD) δ ppm 6.66 (d, J=7.05 Hz, 1 H), 7.18 (d, J=7.05 Hz, 1 H), 7.66 (s, 1 H) 7.67 (d, J=2.01 Hz, 1 H), 8.24 (d, J=2.27 Hz, 1 H); ¹³C NMR (101 MHz, DMSO-D₆) δ ppm 104.05, 125.62, 127.21, 128.54, 129.52, 130.77, 132.43, 136.55, 160.72; LC/MS, MS m/z (M+H)⁺ 180.

References:

BRISTOL-MYERS SQUIBB COMPANY;SUN, Li-Qiang;SCOLA, Paul Michael WO2012/166459, 2012, A1 Location in patent:Page/Page column 23-24