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

HRID 1934921
Notes
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Reaction equation

HRID 1934921 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-4f854e02726a4bf3b5f84e05e395ec92
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06384051B1

Reaction notes

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