2-Fluoro-4-nitrobenzonitrile → 4-(Aminomethyl)-3-fluoroaniline
Reaction equation
[F:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>CO.Cl.[Pd]>[NH2:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:2]=1[F:1]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 2-fluoro-4-nitrobenzonitrile (0.541 g, 2.43 mmol) in methanol (20 mL) and 6N hydrochloric acid (3 mL) was hydrogenated (55 psi) over 10% palladium on carbon (164 mg) for 22 h. The reaction mixture was filtered and concentrated in vacuo to afford 77A (0.65 g, 100%). 1H NMR (400 MHz, CD3OD) δ 4.23 (s, 2H), 7.29 (d, J=8.79 Hz, 2H), 7.68 (t, J=7.91 Hz, 1H).
Workup
- customfor 22 h
- filtrationThe reaction mixture was filtered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c29542fe78c5444db7f11ad1856344cc
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622585B2
Reaction notes
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