N,N-Dimethylaniline → ethyl 4-acetamido-3-nitrobenzoate

HRID 2229447Notes

Reaction equation

HRID 2229447 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18].CN(C)C1C=CC=CC=1.C1(C)C=CC=CC=1>O>[C:1]([NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 1140TolueneHCID 6367Acetyl chlorideHCID 3018687Benzoic acid, 4-amino-3-nitro-, ethyl ester

Product 1

HCID 2826598ethyl 4-acetamido-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Acetyl chloride (62 ml) was added dropwise to a mixture of ethyl 4-amino-3-nitrobenzoate (142 g), N,N-dimethylaniline (110 ml), and toluene (940 ml) in an ice bath. After stirring the mixture at 50° C. for 3 hours, it was cooled. Water (142 ml) was added thereto to stop the reaction. The toluene layer was separated and the organic layer was washed with dilute hydrochloric acid and successively with water. After the organic layer was concentrated to about 1/3 volume, hexane (284 ml) was added thereto for crystallization. Crystals were collected by filtration and washed with hexane to obtain the desired compound, ethyl 4-(acetylamino)-3-nitrobenzoate (157.7 g).

Workup

  1. temperatureit was cooled
  2. customthe reaction
  3. customThe toluene layer was separated
  4. washthe organic layer was washed with dilute hydrochloric acid and successively with water
  5. concentrationAfter the organic layer was concentrated to about 1/3 volume, hexane (284 ml)
  6. additionwas added
  7. customfor crystallization
  8. filtrationCrystals were collected by filtration
  9. washwashed with hexane

Sources & evidence

ORD record
ord-e018559eb664419b8a2ae99d10378e22
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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