1-Fluoro-5-methoxy-2-methyl-4-nitrobenzene → 4-Fluoro-2-methoxy-5-methylaniline

HRID 2229554Notes

Reaction equation

HRID 2229554 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-])=O)=[CH:4][C:3]=1[CH3:13]>C(O)C.[Pd]>[F:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([NH2:10])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

4

Reactant 1

HCID 184681411-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

Product 1

HCID 184681504-Fluoro-2-methoxy-5-methylanilineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-fluoro-5-methoxy-2-methyl-4-nitro-benzene (5.5 g, 29.3 mmol) and 10% Pd-C (1.56 g) in ethanol (300 mL, 0.1 M) was hydrogenated at 1 atm. After stirring overnight, the solution was flushed through a pad of silica gel using 400 mL of ethanol as the eluant. The filtrate was concentrated under reduced pressure to afford 4-fluoro-2-methoxy-5-methyl-phenylamine (4.5 g, 99%) as a pale purple solid: mp 108-110° C.; Rf 0.35 (30% ethyl acetate in heptane); 1H NMR (DMSO-d6, 300 MHz) δ 6.62 (d, J=11.4 Hz, 1H)', 6.43 (d, J=7.8 Hz, 1H), 3.70 (s, 3H), 2.02 (d, J=1.8 Hz, 3H); ESI-LC/MS m/z calcd for C8H10FNO: 155.1; Found 156.0 (M+1)+. Anal. calcd for C8H10FNO: C, 61.92; H, 6.50. Found: C, 61.64; H, 6.53.

Workup

  1. customthe solution was flushed through a pad of silica gel using 400 mL of ethanol as the eluant
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-47f0396483354639961c325bfcc13dc2
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

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