3-Fluoro-4-methyl-5-nitrobenzoic acid → 3-Amino-5-fluoro-4-methylbenzoic acid

HRID 34588Notes

Reaction equation

HRID 34588 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:12]([O-])=O)[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6]>O1CCOCC1.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH2:12])[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 212982453-Fluoro-4-methyl-5-nitrobenzoic acid

Product 1

HCID 212982503-Amino-5-fluoro-4-methylbenzoic acidYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

520 g of 3-fluoro-4-methyl-5-nitro-benzoic acid are hydrogenated in 3,500 ml of dioxane with 50 g of Pd-C catalyst (5% strength) at 50° C. and under 30 bar. The catalyst is then filtered off with suction and the solution is concentrated. 403 g of 3-fluoro-4-methyl-5-amino-benzoic acid are obtained as crude material.

Workup

  1. filtrationThe catalyst is then filtered off with suction
  2. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-1184242b8cd44410a0e50e44896bc021
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Reaction notes

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