Ethanol → 4-Amino-5-fluoro-2-methoxybenzoic acid

HRID 630410Notes

Reaction equation

HRID 630410 reaction equation
[NH2:1][C:2]1[C:9]([F:10])=[CH:8]C(C#N)=[C:4]([O:11][CH3:12])[CH:3]=1.[OH-:13].[Na+].[CH2:15]([OH:17])[CH3:16]>>[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:16]([C:15]([OH:13])=[O:17])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 185196344-Amino-5-fluoro-2-methoxybenzonitrile2×

Product 1

HCID 674693384-Amino-5-fluoro-2-methoxybenzoic acidYield 80%

Conditions

Temperature
110 °C

Procedure

To a solution of 4-amino-5-fluoro-2-methoxybenzonitrile (intermediate 88; 5.3 g, 0.03 mol) in ethanol (20 mL) was added sodium hydroxide 8M (27.9 mL, 0.22 mol), the mixture was placed in a sealed vessel and heated to 110° C. for 20 hours. The solvent was removed under reduced pressure and the crude obtained was partitioned between water and ether. The aqueous layer was acidified by hydrochloric acid 6N until pH 4 and the crude was extracted with ethyl acetate, dried, filtered and evaporated under reduced pressure giving the title compound as a yellow solid (80%), which was used in the next step without further purification.

Workup

  1. customthe mixture was placed in a sealed vessel
  2. customThe solvent was removed under reduced pressure
  3. customthe crude obtained
  4. customwas partitioned between water and ether
  5. extractionthe crude was extracted with ethyl acetate
  6. customdried
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b494ab6197e44209931d40c7e221138b
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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