Acetic Acid → 4-Amino-2-fluoro-5-methoxybenzoic acid

HRID 914221Notes

Reaction equation

HRID 914221 reaction equation
C([C:3]1[C:4]([F:17])=[C:5]([CH:9]=[C:10]([O:15][CH3:16])[C:11]=1[N+:12]([O-])=O)[C:6]([OH:8])=[O:7])C.CC(O)=O>CO>[NH2:12][C:11]1[C:10]([O:15][CH3:16])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:17])[CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86635896HCID 86635896, compound

Product 1

HCID 529829634-Amino-2-fluoro-5-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-fluoro-5-methoxy-4-nitrobenzoic acid (217 mg, 1 mmol), HOAc (cat.) and MeOH (10 mL) was hydrogenated using H-cube hydrogenator. The solution was then concentrated and dried to give the product which can be used for next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.76 (s, 3H) 5.88 (br s, 2H) 6.36 (d, J=16 Hz, 1H) 7.13 (d, J=8 Hz, 1H) 12.32 (br s, 1H).

Workup

  1. concentrationThe solution was then concentrated
  2. customdried
  3. customto give the product which
  4. customcan be used for next step without further purification

Sources & evidence

ORD record
ord-a01e6e046f674735b4ded1fdc32d3c34
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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