Cyclopropanemethanamine → HCID 29274404, compound

HRID 386867Notes

Reaction equation

HRID 386867 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH:12]1([CH2:15][NH2:16])[CH2:14][CH2:13]1.C(N(CC)C(C)C)(C)C>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:16][CH2:15][CH:12]2[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 29274404HCID 29274404, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
96 °C

Procedure

A mixture of 4-bromo-1-fluoro-2-nitrobenzene (9.25 g, 42 mmol), cyclopropanemethylamine (4.49 g, 63.1 mmol) and N,N-diisopropylethylamine (13.5 g, 105 mmol) in ethanol (100 mL) is stirred at 96° C. for 15 h. After cooling to room temperature, the mixture is concentrated under reduced pressure. The residue is purified by column chromatography (silica, eluent: ethyl acetate) to give 11.96 g of 4-bromo-N-(cyclopropylmethyl)-2-nitroaniline. Yield 100%, ES-MS: 271/273 [M+H].

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customThe residue is purified by column chromatography (silica, eluent: ethyl acetate)

Sources & evidence

ORD record
ord-725bc0fa051a4abf8851b4e9a2ef63e2
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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