O-tert-butylhydroxylamine hydrochloride → HCID 86673023, compound

HRID 1853252Notes

Reaction equation

HRID 1853252 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH:7]=[C:8]([C:12]3[N:13]=[CH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:9]2)=[CH:4][C:3]=1[CH3:23].Cl.[C:25]([O:29][NH2:30])([CH3:28])([CH3:27])[CH3:26]>CO>[C:25]([O:29][N:30]=[C:6]1[C:5]2[C:10](=[CH:11][C:2]([Br:1])=[C:3]([CH3:23])[CH:4]=2)[O:9][C:8]([C:12]2[N:13]=[CH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:7]1)([CH3:28])([CH3:27])[CH3:26].[C:25]([O:29][N:30]=[C:6]1[C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[O:9][C:8]([C:12]2[N:13]=[CH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:7]1)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 2

HCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 67194821HCID 67194821, compound

Product 2

HCID 86673023HCID 86673023, compoundYield 91.4%HCID 86673025HCID 86673025, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-bromo-2-isoquinolin-3-yl-6-methyl-chromen-4-one O-tert-butyl oxime was prepared using the method D (step 1) illustrated in example 1B. 7-bromo-2-isoquinolin-3-yl-6-methyl-chromen-4-one (730 mg, 1.98 mmol) was treated with O-tert-butyl-hydroxylamine hydrochloride (500 mg, 3.98 mmol) in methanol (13 ml) under microwave irradiation to yield 7-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (383 mg, 44%) as a yellow solid after purification by flash chromatography over silica gel (cyclohexane/Chloroform/ethyl acetate: 96/4/0; 50/50/0; 0/100/0 0/50/50).

Sources & evidence

ORD record
ord-b7a4af8804a04b07a5d8721aa46795ad
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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