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Dimethylformamide → Anthranilic acid, N-dimethylaminomethylene-, methyl ester

HRID 1595722
Notes
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Reaction equation

HRID 1595722 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[CH3:19][N:20]([CH3:23])[CH:21]=O>ClCCl>[CH3:19][N:20]([CH:23]=[N:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8635Methyl AnthranilateHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride

Product 1

HCID 13058944Anthranilic acid, N-dimethylaminomethylene-, methyl ester

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
On this pageParticipantsProcedureWorkupSources & evidenceReaction notes
Solvent

Procedure

To a stirred solution of 7.56 g of methyl anthranilate in 50 ml of dimethylformamide at 0° C. was added 5.6 ml of phosphorous oxychloride during 15 m. The mixture was heated at 55 for 45 m, cooled to 0, and diluted with dichloromethane. The mixture was basified at 0° C. by slow addition of cold 1N NaOH to pH 9. The dichloromethane layer was separated, washed with water, dried and concentrated to an oil.

Workup

  1. temperatureThe mixture was heated at 55 for 45 m
  2. temperaturecooled to 0
  3. customThe dichloromethane layer was separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-e8a60b800d404bacb268e5c3beefec69
Source dataset
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06288082B1

Reaction notes

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