Phosphorus oxychloride → HCID 86683270, compound

HRID 1852252Notes

Reaction equation

[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=O)[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=3)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:13]1[C:14]2[C:19](=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=2)[CH:20]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=2)[N:12]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 70978446HCID 70978446, compound

Product 1

HCID 86683270HCID 86683270, compoundYield 67.4%

Procedure

A solution of 3-(4-isopropoxyphenyl)-6-methoxyisoquinolin-1(2H)-one (3.5 g, 11.31 mmol) in POCl3 (11 ml) was refluxed for overnight. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (10% ethyl acetate in pet ether) to get desired compound (2.5 g, 67.4%) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.06-8.04 (d, J=8 Hz, 1H), 8.03-8.01 (d, J=8 Hz, 2H), 7.81 (s, 1H), 7.22-7.20 (d, J=8 Hz, 1H), 7.00 (s, 1H), 6.99-6.97 (d, J=8 Hz, 1H), 4.63 (m, 1H), 3.96 (s, 3H), 1.38 (m, 6H).

Workup

customThe solvent was evaporated under reduced pressure
additionthe residue was diluted with cold water
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customto get crude compound
customThe crude compound was purified by silica gel chromatography (10% ethyl acetate in pet ether)

Sources & evidence

ORD record: ord-b4ef000ef1f14e78baa9fef26e7d6fc6
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957203B2

Reaction notes

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