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

HRID 1880856Notes

Reaction equation

HRID 1880856 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CC(O)=O.[H][H]>CO>[NH2:11][C:9]1[C:8]([O:14][CH3:15])=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 579556142-Fluoro-5-methoxy-4-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 529829634-Amino-2-fluoro-5-methoxybenzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-fluoro-5-methoxy-4-nitrobenzoic acid (10 g, 46 mmol), HOAc (50 mL) and MeOH (50 mL) was hydrogenated using a hydrogen balloon overnight. The solution was then filtered through celite and concentrated to a residue, which was triturated with ether and ethyl acetate. The solid was filtered and dried to give the product as light yellow powder (8.3 g, 98%). 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). [M+H] calc'd for C8H8FNO3, 186; found 186.

Workup

  1. filtrationThe solution was then filtered through celite
  2. concentrationconcentrated to a residue, which
  3. customwas triturated with ether and ethyl acetate
  4. filtrationThe solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-549fdeb6d285498aba109c032741056f
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

Loading…