O-tert-butylhydroxylamine hydrochloride → HCID 86673021, compound

HRID 1853248Notes

Reaction equation

HRID 1853248 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[O:12][C:13]3[C:18]([C:19](=O)[CH:20]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:2]=1.Cl.[C:23]([O:27][NH2:28])([CH3:26])([CH3:25])[CH3:24]>CO>[C:23]([O:27][N:28]=[C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12][C:11]([C:3]2[N:2]=[CH:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)=[CH:20]1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 67193464HCID 67193464, compound

Product 1

HCID 86673021HCID 86673021, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of 2-isoquinolin-3-yl-chromen-4-one (459 mg, 1.67 mmol) in methanol (11 ml) was added O-tert-butyl hydroxylamine hydrochloride (421 mg, 3.35 mml). The mixture was heated to 130° C. under microwave irradiation for 30 min. The volatiles were removed by vacuum distillation and the residue was purified by flash chromatography (cyclohexane/ethyl acetate 95/5) to yield 2-isoquinolin-3-yl-chromen-4-one O-tert-butyl-oxime (387 mg, 67%) as a yellow solid.

Workup

  1. customThe volatiles were removed by vacuum distillation
  2. customthe residue was purified by flash chromatography (cyclohexane/ethyl acetate 95/5)

Sources & evidence

ORD record
ord-941ad5739a154eefbe2d42559bd554b7
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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