N,N-Dimethylaniline → Benzamide, 2-hydroxy-N-(4-methoxyphenyl)-4-methyl-

HRID 616194Notes

Reaction equation

HRID 616194 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:11]C(=O)C)[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1.CN(C)C1C=CC=CC=1>CC(C)=O>[OH:11][C:4]1[CH:3]=[C:2]([CH3:1])[CH:10]=[CH:9][C:5]=1[C:6]([NH:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[O:8]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 7732P-AnisidineHCID 1527825814504-07-5

Product 1

HCID 3047112Benzamide, 2-hydroxy-N-(4-methoxyphenyl)-4-methyl-Yield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

4-Methyl-acetylsalicylic acid (5 g.) was converted to its acid chloride by a conventional method and dissolved in acetone (200 ml.). Then p-anisidine (3.2 g.) and dimethylaniline (3.1 g.) were dissolved in acetone (100 ml.) and the above acid chloride solution was added by drops while cooling and mixing; agitation was maintained for 1 to 2 hours. Then the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate and treated as in the similar method of Example 5 to give 2-hydroxy-4-methyl-4'-methoxybenzanilide (5.3 g.). Yield: 80%, melting point: 185°-186° C.

Workup

  1. temperaturewhile cooling
  2. additionmixing
  3. temperatureagitation was maintained for 1 to 2 hours
  4. concentrationThen the reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. additiontreated as in the similar method of Example 5

Sources & evidence

ORD record
ord-cce04ac133a547d5874e9764cbc017ea
Source dataset
uspto-grants-1978_02
Patent number
US04072753

Reaction notes

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