Cyclopropylamine → 5-Bromo-N-cyclopropyl-2-nitrobenzenamine

HRID 1048968Notes

Reaction equation

HRID 1048968 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.CC[N:14]([CH:18]([CH3:20])[CH3:19])C(C)C.C1(N)CC1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:14][CH:18]2[CH2:20][CH2:19]2)[CH:3]=1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 653413525-Bromo-N-cyclopropyl-2-nitrobenzenamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 4-bromo-2-fluoronitrobenzene (2M g, 0.0091 mol) in DMF (10 ml) was added carefully DIPEA (3.25 ml, 0.0182 mol) and cyclopropylamine (0.7 ml, 0.0091 mol) and the resulting solution was stirred at room temperature for 14 h. The reaction was quenched with ice-water and extracted with diethyl ether (3×100 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated under vacuum to afford the title compound (5-bromo-2-nitro-phenyl)-cyclopropylamine as a yellow solid. C9H9BrN2O2; 1H NMR (400 MHz, DMSO-d6), δ: 8.08 (brs, 1H), 8.02-7.99 (d, J=8.8 Hz, 1H), 7.47 (s, 1H), 7.26 (s, 1H), 6.82-6.79 (dd, J=8.8 Hz, 1.6 Hz, 1H), 2.58-2.54 (m, 1H), 0.97-0.88 (m, 2H), 0.69-0.65 (m, 2H). MS (M+1): 258.

Workup

  1. customThe reaction was quenched with ice-water
  2. extractionextracted with diethyl ether (3×100 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-747dfa2c4ab84fd49a1cd3feb3a187eb
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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