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

HRID 2036591Notes

Reaction equation

HRID 2036591 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[F:11].[CH:12]1([NH2:15])[CH2:14][CH2:13]1>C1COCC1.CCOC(C)=O>[CH:12]1([NH:15][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=2[F:11])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 183734742-Bromo-1-fluoro-3-nitrobenzene

Product 1

HCID 58459337N-cyclopropyl-2-fluoro-6-nitroaniline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-bromo-1-fluoro-3-nitrobenzene (2.0 g, 9.1 mmol), cyclopropanamine (1.26 mL, 18.2 mmol) in THF (10 mL) under N2 was heated at 60° C. for 4 days. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on a silica gel column using hexane-EtOAc (8.5:1.5) as eluent to give N-cyclopropyl-2-fluoro-6-nitroaniline.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on a silica gel column

Sources & evidence

ORD record
ord-fdfdd89b585e45b38ccf0ea03b007305
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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