5-Fluoro-4-methyl-2-nitrobenzoic acid → 2-Amino-5-fluoro-4-methylbenzoic acid

HRID 34591Notes

Reaction equation

HRID 34591 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([CH3:13])[C:10]([F:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O>O1CCOCC1.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]([CH3:13])[C:10]([F:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 136574495-Fluoro-4-methyl-2-nitrobenzoic acid

Product 1

HCID 136574502-Amino-5-fluoro-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

525 g of 2-nitro-4-methyl-5-fluoro-benzoic acid are hydrogenated in 3 l of dioxane with 50 g of 5% strength Pd-C catalyst at 30°-40° under 20-30 bar. The catalyst is filtered off with suction and the solution is poured onto water. The crystals which have precipitated are filtered off with suction and dried. Yield: 357 g (80.1% of theory), melting point: 201°-202° C.

Workup

  1. filtrationThe catalyst is filtered off with suction
  2. additionthe solution is poured onto water
  3. customThe crystals which have precipitated
  4. filtrationare filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-e46f2afba65f4f8c8a73c8e0d2d83634
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Reaction notes

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