3-Bromoaniline → HCID 58109514, compound

HRID 2037408Notes

Reaction equation

HRID 2037408 reaction equation
C[N:2]([CH3:13])[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[Br:14][C:15]1[CH:16]=C([CH:19]=[CH:20][CH:21]=1)N>CCO.O>[Br:14][C:15]1[CH:16]=[C:13]([NH:2][CH2:3][CH2:4][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6])[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 770423-(Dimethylamino)-1-phenyl-1-propanone

Product 1

HCID 58109514HCID 58109514, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(dimethylamino)-1-phenylpropan-1-one (0.1 mol) and 3-bromoaniline (0.1 mol) in 1:1 EtOH/H2O (100 mL) was heated at 80° C. overnight. The resulting mixture was concentrated and the residue was washed with H2O and then EtOH several times to give to give 3-(3-bromophenylamino)-1-phenylpropan-1-one (27 g, 90%). 1H NMR (400 MHz, CDCl3): δ=3.52 (m, 2H), 4.33 (m, 2H), 4.51 (m, 1H), 6.8 (m, 1H), 7.05 (m, 2H), 7.28 (m, 1H), 7.72 (m, 2H), 7.80 (m, 1H), 8.2 (m, 2H).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. washthe residue was washed with H2O
  3. customEtOH several times to give

Sources & evidence

ORD record
ord-7a7d3e5c6ed54f088869efd92be90f0e
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…