2-fluoro-3-methoxy-N-methyl-6-nitroaniline → 3-fluoro-4-methoxy-N2-methylbenzene-1,2-diamine

HRID 882204Notes

Reaction equation

HRID 882204 reaction equation
[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]([N+:12]([O-])=O)[C:3]=1[NH:4][CH3:5]>C(O)(=O)C.[Fe]>[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]([NH2:12])[C:3]=1[NH:4][CH3:5]

Participants

4

Reactant 1

HCID 667492842-fluoro-3-methoxy-N-methyl-6-nitroaniline

Product 1

HCID 667491243-fluoro-4-methoxy-N2-methylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-fluoro-3-methoxy-N-methyl-6-nitroaniline (7-2, 1.04 g, 5.20 mmol) in Acetic acid (25 ml) was charged with Iron (powder). The resulting mixture was stirred at 23 deg C. for 22 h. The reduced material concentrated in vacuo, and the residual oil was taken up in Methylene Chloride and filtered through Celite. The filtrate was again concentrated in vacuo, leaving the title compound, 3-fluoro-4-methoxy-N2-methylbenzene-1,2-diamine (7-3), as a maroon oil with >80% purity. LRMS m/z: Calc'd for C8H11FN2O (M+H) 171.2, found 170.9.

Workup

  1. concentrationThe reduced material concentrated in vacuo
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was again concentrated in vacuo

Sources & evidence

ORD record
ord-50dac30034da4218bb8e8deced8d019b
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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