3-Bromoaniline → HCID 67152351, compound

HRID 2064115Notes

Reaction equation

HRID 2064115 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(N(C(C)C)CC)(C)C.[Br:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>CN1C(=O)CCC1.O>[Br:22][C:23]1[CH:24]=[C:25]([NH:26][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 115623-BromoanilineHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 81531Diisopropylethylamine

Product 1

HCID 67152351HCID 67152351, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-chloro-3-nitrobenzonitrile (A) (5 g, 27.4 mmol) and diisopropyl-ethylamine (4.24 g, 32 mmol) in NMP (40 mL) was added 3-bromoaniline (B) (4.71 g, 27.4 mmol) and the reaction mixture was stirred at 80° C. for 6 h. The reaction mixture was cooled to RT and diluted with water. The solid was filtered off, washed several times with water to remove excess 3-bromoaniline, dried under vacuum to give compound C (5.8 g, 66%) as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationThe solid was filtered off
  3. washwashed several times with water
  4. customto remove excess 3-bromoaniline
  5. customdried under vacuum

Sources & evidence

ORD record
ord-03473e27d4ef454389d1453f2fe7dd91
Source dataset
uspto-grants-2012_10
Patent number
US08288418B2

Reaction notes

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