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

HRID 1880992Notes

Reaction equation

HRID 1880992 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, 3 H) 5.88 (br s, 2 H) 6.36 (d, J=16 Hz, 1 H) 7.13 (d, J=8 Hz, 1 H) 12.32 (br s, 1 H).

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-a646ff95ef594382a85f0349a5587680
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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