P-Anisidine → 2-amino-N-(4-methoxy-phenyl)-3-methoxy-benzamide

HRID 617128Notes

Reaction equation

HRID 617128 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[NH:9]C(O[C:13](=[O:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=O.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1>C(O)C.CN(C)C1C=CN=CC=1>[NH2:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=1[C:13]([NH:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[O:14]

Participants

5

Reactant 2

HCID 7732P-AnisidineHCID 105596798-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

Product 1

HCID 181744302-amino-N-(4-methoxy-phenyl)-3-methoxy-benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Procedure

To a solution of 27.17 g (0.141 mol) of 8-methoxyisatoic anhydride in 200 mL of ethanol was added a catalytic amount of 4-dimethylaminopyridine and 350 mL of a 1M solution containing 43.0 g (0.350 mol) of p-anisidine. The reaction mixture was stirred and heated under reflux overnight. The reaction flask was then chilled on ice. The precipitate that formed was collected by vacuum filtration and amounted to 34.7 g. An analytical sample (mp 168-169° C.) was obtained by recrystallization from ethanol.

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. temperatureThe reaction flask was then chilled on ice
  4. customThe precipitate that formed
  5. filtrationwas collected by vacuum filtration
  6. customAn analytical sample (mp 168-169° C.) was obtained by recrystallization from ethanol

Sources & evidence

ORD record
ord-f72bda8dcd30406794af07be74c69540
Source dataset
uspto-grants-1999_09
Patent number
US05948775

Reaction notes

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