3,4-Dimethylaniline → HCID 66965255, compound

HRID 1514972Notes

Reaction equation

HRID 1514972 reaction equation
[OH: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.O>[CH3:35][C:36]1[CH:37]=[C:38]([NH:39][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)[CH:40]=[CH:41][C:42]=1[CH3:43]

Participants

7

Reactant 4

HCID 72483,4-DimethylanilineHCID 120334-Hydroxy-3-nitrobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 66965255HCID 66965255, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-hydroxy-3-nitrobenzoic acid (732 mg), EDCI (768 mg) and HOBt (540 mg) in DMF (8 mL) was added 3,4-dimethylaniline (484 mg) and the mixture was stirred at room temperature for 18 h. The mixture was poured into water and was extracted with EtOAc. The organic phase was washed with water (3×) and dried over sodium sulfate. The solvent was concentrated until crystallization occurred. The mixture was cooled to room temperature and the solid filtered, washed with EtOAc and dried under reduced pressure to give N-(3,4-dimethyl-phenyl)-4-hydroxy-3-nitrobenzamide as a pale-yellow solid, mp=209-212° C.; MS (m/z) 285 (M−1).

Workup

  1. extractionwas extracted with EtOAc
  2. washThe organic phase was washed with water (3×)
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solvent was concentrated until crystallization
  5. temperatureThe mixture was cooled to room temperature
  6. filtrationthe solid filtered
  7. washwashed with EtOAc
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-37e78e71a6f24aaa9c46595bbc6d3942
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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