7-CHLORO-1-HYDROXYISOQUINOLINE Chemical Properties

Melting point:

245-247 °C(Solv: methanol (67-56-1))

Boiling point:

414.9±45.0 °C(Predicted)

Density 

1.339±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

11.99±0.20(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C9H6ClNO/c10-7-2-1-6-3-4-11-9(12)8(6)5-7/h1-5H,(H,11,12)

InChIKey

YWUCOQGBXQHOJM-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC(Cl)=C2)C=CN1

Safety Information

HS Code 

2933499090

7-CHLORO-1-HYDROXYISOQUINOLINE Usage And Synthesis

Uses

7-Chloroisoquinolin-1(2H)-one acts as a reagent for the preparation, SAR of methoxyisoquinoline derivative and discovery of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor for the treatment of hepatitis C virus infection. Synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists.

Synthesis

Step 1: Diphenyl phosphate azide (DPPA, 27.5 g, 0.1 mol) was added dropwise to a solution of (E)-3-(4-chlorophenyl)acrylic acid (18.3 g, 0.1 mol) and triethylamine (Et3N, 20.2 g, 0.2 mol) in benzene (100 mL). After stirring the reaction mixture for 2 h, the solution was concentrated and purified by fast chromatography (Biotage system, mobile phase 20/80 ethyl acetate/hexane) to give 16 g of the intermediate azide as a solid. The intermediate was dissolved in 100 mL of 1,2-dichloroethane and the resulting mixture was slowly heated to 90 °C over 30 min. The reaction mixture was then heated to reflux and held at this temperature for 3 hours. After cooling to room temperature, a solid was precipitated, collected by filtration and washed with toluene to give 9.5 g of 7-chloroisoquinolin-1(2H)-one in 53% yield. Product characterization data. 1H NMR (400 MHz, CD3OD) δ ppm: 6.66 (d, J = 7.05 Hz, 1H), 7.18 (d, J = 7.05 Hz, 1H), 7.66 (s, 1H), 7.67 (d, J = 2.01 Hz, 1H), 8.24 (d, J = 2.27 Hz, 1H). 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

[1] Patent: WO2012/166459, 2012, A1. Location in patent: Page/Page column 23-24

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