N-cyclopropyl-2-fluoro-6-nitroaniline → N1-cyclopropyl-6-fluorobenzene-1,2-diamine

HRID 2036592Notes

Reaction equation

HRID 2036592 reaction equation
[CH:1]1([NH:4][C:5]2[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:6]=2[F:14])[CH2:3][CH2:2]1>CO>[CH:1]1([NH:4][C:5]2[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:6]=2[F:14])[CH2:3][CH2:2]1

Participants

3

Reactant 1

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

Product 1

HCID 58459112N1-cyclopropyl-6-fluorobenzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-cyclopropyl-2-fluoro-6-nitroaniline (650 mg, 3.31 mmol) in MeOH (15 mL) palladium 10 wt % on carbon (176 mg, 0.166 mmol) was added under N2. After flushing the flask with N2 for two minutes, the solution was stirred under a H2 balloon. After 6 h, the mixture was filtered through a celite pad rinsed with MeOH, and concentrated under reduced pressure. The residue was purified by column chromatography on a silica gel column using EtOAc:DCM (1:1) as eluent to give N1-cyclopropyl-6-fluorobenzene-1,2-diamine: LC-MS (ESI) m/z 167.1 [M+H]+.

Workup

  1. customAfter flushing the flask with N2 for two minutes
  2. filtrationthe mixture was filtered through a celite pad
  3. washrinsed with MeOH
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on a silica gel column

Sources & evidence

ORD record
ord-4a91c4fa528e4a9d8aa8d04af50d9e01
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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