Sodium Hydroxide → HCID 136352217, compound

HRID 1853249Notes

Reaction equation

C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:10][C:9]([C:17]2[N:18]=[CH:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:8]1)(C)(C)C.[OH-].[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[C:17]([C:9]2[O:10][C:11]3[C:16]([C:7](=[N:6][OH:5])[CH:8]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice cooled solution of 2-isoquinolin-3-yl-chromen-4-one O-tert-butyl-oxime (136 mg, 0.39 mmol) in dichloromethane (10 ml) was cautiously added dropwise a 1M solution of titanium tetrachloride in dichloromethane (1.2 ml, 1.2 mmol). The mixture was stirred at 0° C. 2 hours, then at room temperature 2 more hours and poured onto ice cold water (100 ml). The mixture was basified using a 6N aqueous sodium hydroxide solution until pH 10 and the yellow precipitate was collected by filtration. The solid was washed with water, dried and purified by flash chromatography (cyclohexane/ethyl acetate/dichloromethane:80/10/10; 60/30/10 then 0/50/50) to yield 2-isoquinolin-3-yl-chromen-4-one oxime (71 mg, 62%) as a yellow solid. The product was isolated as a 95/5 mixture of Z/E oxime isomers.

Workup

addition2 hours, then at room temperature 2 more hours and poured onto ice cold water (100 ml)
filtrationthe yellow precipitate was collected by filtration
washThe solid was washed with water
customdried
custompurified by flash chromatography (cyclohexane/ethyl acetate/dichloromethane

Sources & evidence

ORD record: ord-1cd4fd829f4641298b1f74fea7136aee
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962627B2

Reaction notes

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