Methylamine → 5-bromo-N-methyl-2-nitroaniline

HRID 1186087Notes

Reaction equation

HRID 1186087 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.CN.C[CH2:15][N:16](C(C)C)C(C)C>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[NH:16][CH3:15]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 106095305-bromo-N-methyl-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

4-Bromo-2-fluoronitrobenzene (Aldrich, 1 eqvt), methylamine (2 eqvt), and hunig's base (3 eqvt) in DMF (1 Molar in substrate) were placed in a sealed vial and heated to 85° C. overnight. The crude mixture was diluted with water, and the product collected by filtration. Purification by chromatography (gradient: 92:8 hexanes:ethyl acetate to 68:32 hexanes:ethyl acetate) provided the title compound. 1HNMR (DMSO-d6, 400 MHz) δ 8.22 (bd, J=4.4 Hz, 1H), 7.95 (d, J=8.8 Hz, 1H), 7.14 (d, J=2 Hz, 1H), 6.80 (dd, J=9.2, 2.4 Hz, 1H), 2.92 (d, J=4.8 Hz).

Workup

  1. filtrationthe product collected by filtration
  2. customPurification by chromatography (gradient: 92:8 hexanes:ethyl acetate to 68:32 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-28383e43e0d8473290bc61d11ffb7cdd
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

Loading…