Hydrochloric Acid → 4-Amino-2-chloro-3-fluorobenzoic acid

HRID 1878364Notes

Reaction equation

HRID 1878364 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8]C(C#N)=[C:4]([Cl:10])[C:3]=1[F:11].[OH-:12].[Na+].[CH2:14]([OH:16])[CH3:15].Cl>C(OCC)(=O)C>[NH2:1][C:2]1[CH:9]=[CH:8][C:15]([C:14]([OH:12])=[O:16])=[C:4]([Cl:10])[C:3]=1[F:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 534162084-Amino-2-chloro-3-fluorobenzonitrile

Product 1

HCID 668788144-Amino-2-chloro-3-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Amino-2-chloro-3-fluorobenzonitrile (500 mg, 2.93 mmol) and sodium hydroxide (4M, 18 mL) were mixed with ethanol (8 mL) and heated to reflux for 18 hours. After this time the mixture was allowed to cool to room temperature and 1M hydrochloric acid was added until pH 1 was achieved. Ethyl acetate was added and the organic layer was separated and washed with water and brine. The organic phase was dried with sodium sulfate, filtered and concentrated under vacuum to give the title compound (500 mg),

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. customthe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-95ab18b4d2cf426ba9dac926435ff772
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

Loading…