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O-Methylhydroxylamine hydrochloride → 6-Chloro-2-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid

HRID 750180
Notes
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Reaction equation

HRID 750180 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[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.Cl.[CH3:23][O:24][NH2:25].C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:25]([O:24][CH3:23])[C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 103800926-chloro-4-phenylisocoumarin-3-carboxylic AcidHCID 10942334Sodium Methoxide

Product 1

HCID 230609396-Chloro-2-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Chloro-1-oxo-4-phenyl-1H-isochromen-3-carboxylic acid (150 mg) was dissolved in methanol (3.0 ml) and O-methylhydroxylamine hydrochloride (420 mg) and sodium methoxide (270 mg) were added. The mixture was stirred at room temperature for 12 hrs. and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and 1N hydrochloric acid, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure to dryness. Then, 4N hydrochloric acid ethyl acetate solution (3 ml) was added to the residue and the mixture was stirred at room temperature for 12 hrs. Water was added to wash the reaction mixture, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 6-chloro-2-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid.

Workup

  1. concentrationand concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure to dryness
  5. additionThen, 4N hydrochloric acid ethyl acetate solution (3 ml) was added to the residue
  6. stirringthe mixture was stirred at room temperature for 12 hrs
  7. additionWater was added
  8. washto wash the reaction mixture
  9. dry with materialthe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e1fb45fe558468294b5dc3035649200
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07402595B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes