3-Chloro-4-fluoroaniline → HCID 14076517, compound

HRID 2413955Notes

Reaction equation

HRID 2413955 reaction equation
[C:1]1(=[O:6])[O:5][CH:3]([CH3:4])[CH2:2]1.[Cl:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][C:14]=1[F:15])[NH2:11]>CCOCC>[Cl:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][C:14]=1[F:15])[NH:11][CH:3]([CH3:4])[CH2:2][C:1]([OH:5])=[O:6]

Participants

4

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 18303beta-BUTYROLACTONE

Product 1

HCID 14076517HCID 14076517, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

86 g (1.00 mole) of β-butyrolactone was added to 146 g (1.00 mole) of 3-chloro-4-fluoroaniline, and this mixture was stirred at 80°-90° C. for 30 minutes and then allowed to cool to room temperature. To the resulting reaction solution was added 1000 ml of ether. This mixture was filtered to remove any insoluble matter, and the filtrate thus obtained was extracted with 750 ml of a 2N aqueous solution of sodium hydroxide. This extract was acidified with 130 ml of concentrated hydrochloric acid and then extracted with 1000 ml of ether. The ether layer was separated, dried over anhydrous sodium sulfate and then evaporated to dryness. Thus, there was obtained 111 g (47.9% yield) of 3-(3-chloro-4-fluoro-anilino) butyric acid in the form of pale-yellow oily matter.

Workup

  1. customTo the resulting reaction solution
  2. filtrationThis mixture was filtered
  3. customto remove any insoluble matter
  4. customthe filtrate thus obtained
  5. extractionwas extracted with 750 ml of a 2N aqueous solution of sodium hydroxide
  6. extractionextracted with 1000 ml of ether
  7. customThe ether layer was separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-ecf1d1918ee84b1da5d227ccc3a84722
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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