Acetic Acid → 4-Amino-3-fluoro-5-methoxybenzoic acid

HRID 1880969Notes

Reaction equation

HRID 1880969 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:14][CH3:15])[C:10]=1[N+:11]([O-])=O)[C:5]([OH:7])=[O:6].CC(O)=O.[H][H]>CO>[NH2:11][C:10]1[C:9]([O:14][CH3:15])=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 579555223-Fluoro-5-methoxy-4-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 579556404-Amino-3-fluoro-5-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-fluoro-5-methoxy-4-nitrobenzoic acid (obtained above), HOAc (5 mL) and MeOH (5 mL) was hydrogenated using a hydrogen balloon overnight. The solution was then filtered through celite and concentrated to a red solid (590 mg, 66%). [M+H] calc'd for C8H8FNO3, 186; found 186.

Workup

  1. filtrationThe solution was then filtered through celite
  2. concentrationconcentrated to a red solid (590 mg, 66%)

Sources & evidence

ORD record
ord-e031b782645449e59b532a8bd890201f
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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