O-Benzylhydroxylamine → 2-benzyloxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

HRID 750183Notes

Reaction equation

HRID 750183 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[O:7][C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:22]([O:29][NH2:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C>[CH2:22]([O:29][N:30]1[C:6]([C:13]([OH:15])=[O:14])=[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[C:8]1=[O:7])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 102313O-BenzylhydroxylamineHCID 103800926-chloro-4-phenylisocoumarin-3-carboxylic Acid

Product 1

HCID 230607592-benzyloxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic AcidYield 88.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-chloro-1-oxo-4-phenyl-1H-isochromen-3-carboxylic acid (300 mg), O-benzylhydroxylamine (620 mg) and ethanol (6.0 ml) was stirred at 90° C. for 12 hrs. in a sealed tube. After cooling, the reaction mixture was concentrated under reduced pressure and the residue was washed with ethyl acetate/diethyl ether=1/10 to give the title compound (360 mg) as a colorless powder.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. washthe residue was washed with ethyl acetate/diethyl ether=1/10

Sources & evidence

ORD record
ord-1d270f85e6cc43679b1969c9183bf047
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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