3,4-Dimethylaniline → 4-amino-N-(3,4-dimethylphenyl)-3-nitrobenzamide

HRID 1514979Notes

Reaction equation

HRID 1514979 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:35][C:36]1[CH:37]=[C:38]([NH2:43])[CH:39]=[CH:40][C:41]=1[CH3:42].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:43][C:38]2[CH:39]=[CH:40][C:41]([CH3:42])=[C:36]([CH3:35])[CH:37]=2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

9

Reactant 5

HCID 72483,4-DimethylanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 87439264-amino-N-(3,4-dimethylphenyl)-3-nitrobenzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-amino-3-nitrobenzoic acid (1.82 g) in DMF (20 mL) was added HOBT (1.49 g) and EDCI (2.1 g). After stirring at room temperature for 10 min, 3,4-dimethylphenylamine (1.2 g) and DIPEA (5.3 mL) were added. The solution was stirred at room temperature for 18 h then the mixture was partioned between water and EtOAc The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried, filtered and concentrated. The residue was purified by recrystallization from EtOAc and gave 4-amino-N-(3,4-dimethylphenyl)-3-nitrobenzamide as a yellow solid. MS (ESI)m/z 286 (M+H).

Workup

  1. stirringThe solution was stirred at room temperature for 18 h
  2. extractionwas extracted with EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by recrystallization from EtOAc

Sources & evidence

ORD record
ord-29bcb15f6d4745fda8e136e230a249b0
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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