Cyclopropylamine → 2-bromo-N-cyclopropyl-6-nitroaniline

HRID 2036644Notes

Reaction equation

HRID 2036644 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1F.[CH:12]1([NH2:15])[CH2:14][CH2:13]1>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[NH:15][CH:12]1[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 404274461-Bromo-2-fluoro-3-nitrobenzene

Product 1

HCID 674318802-bromo-N-cyclopropyl-6-nitroaniline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-bromo-2-fluoro-3-nitrobenzene (4.1 g, 18.6 mmol) and cyclopropanamine (1.29 mL, 18.6 mmol) in THF (10 mL) was stirred under N2 at 60° C. for 18 h. The reaction mixture was diluted with EtOAc, washed with water, filtered on a pad of Celite™, washed with brine and dried over magnesium sulfate. The solution was concentrated in vacuo. Purification of the residue by flash chromatography on a silica gel column using 30 to 50% gradient of DCM in hexane as eluent gave 2-bromo-N-cyclopropyl-6-nitroaniline: LC-MS (ESI) m/z 259.0 [M+H]+.

Workup

  1. washwashed with water
  2. filtrationfiltered on a pad of Celite™
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated in vacuo
  6. customPurification of the residue by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-5421217dfa63464cbfcb5236f9efaeb3
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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