2-Fluoro-1-methoxy-3-methyl-4-nitrobenzene → 3-Fluoro-4-methoxy-2-methylaniline

HRID 1962882Notes

Reaction equation

HRID 1962882 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]>C(O)(=O)C.[Fe]>[F:1][C:2]1[C:7]([CH3:8])=[C:6]([NH2:9])[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]

Participants

4

Reactant 1

HCID 667517592-Fluoro-1-methoxy-3-methyl-4-nitrobenzene

Product 1

HCID 667520573-Fluoro-4-methoxy-2-methylaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Iron powder (14.25 g) was added portion wise to a solution of 2-fluoro-1-methoxy-3-methyl-4-nitro-benzene (10.5 g, 90% purity) in acetic acid (350 ml) at room temperature. The resulting brown suspension was stirred during 2 hours at room temperature. The reaction mixture was quenched with concentrated aq NaOH solution and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure to obtain 3-fluoro-4-methoxy-2-methyl-phenylamine as orange oil (8.50 g, 90% purity) which was used in Step 4 without any further purification. 1H NMR (CDCl3) δ ppm: 6.66 (1H, dd); 6.38 (1H, dd); 3.80 (3H, s); 3.34 (2H, br s); 2.08 (3H, d).

Workup

  1. customThe reaction mixture was quenched with concentrated aq NaOH solution
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over sodium sulphate anhydrous
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8aef6bd4b2414a73977b805c4d915c4f
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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