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

HRID 1514889Notes

Reaction equation

HRID 1514889 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].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:35][C:36]1[CH:37]=[C:38]([CH:40]=[CH:41][C:42]=1[CH3:43])[NH2:39]>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:39][C:38]2[CH:40]=[CH:41][C:42]([CH3:43])=[C:36]([CH3:35])[CH:37]=2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

8

Reactant 4

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

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-nitro-benzoic acid (546 mg). EDCI (576 mg) and HOBt (405 mg) in DMF (8 mL) was added 3,4-dimethylaniline (363 mg) and the mixture was stirred at room temperature for 3 h. The mixture was poured into water and exreacted with EtOAc. The organic phase was washed with water (2×) and was dried over sodium sulfate. The solvent was concentrated to approximately 10 mL and the resulting precipitate was filtered, washed with EtOAc and dried under reduced pressure to give 4-amino-N-(3,4-dimethyl-phenyl)-3-nitro-benzamide as a yellow solid, mp=192-195° C.; MS (m/z) 284 (M−1).

Workup

  1. washThe organic phase was washed with water (2×)
  2. dry with materialwas dried over sodium sulfate
  3. concentrationThe solvent was concentrated to approximately 10 mL
  4. filtrationthe resulting precipitate was filtered
  5. washwashed with EtOAc
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-06e33d415b984e159feeaa1077324aab
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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