2-Fluoroaniline → 3-Ethoxy-N-(2-fluorophenyl)-2-propenamide

HRID 1196551Notes

Reaction equation

HRID 1196551 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:9]([O:11][CH:12]=[CH:13][C:14](Cl)=[O:15])[CH3:10]>N1C=CC=CC=1>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:14](=[O:15])[CH:13]=[CH:12][O:11][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 30144293-Ethoxy-2-propenoyl chloride

Product 1

HCID 540943573-Ethoxy-N-(2-fluorophenyl)-2-propenamideYield 17.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-fluoroaniline (ex. Aldrich) (3 g) in pyridine (20 ml) was treated at 0° with 3-ethoxyacryloyl chloride (3.64 g) (Prepared according to Paul et al, U..S. Pat. No. 2,768,174, (1956)). After 30 minutes at 0°-10° the reaction mixture was partitioned between ether and water and worked-up in conventional fashion. Chromatography on silica (ether : hexane, 1:1) gave N-(2-fluorophenyl)-3-ethoxyacrylamide (1 g). The latter was added in portions to conc. sulphuric acid (15 ml) at room temperature. After stirring overnight the mixture was poured onto ice-water. The resultant cream precipitate was collected and dried in vacuo to give 2-hydroxy-8-fluoroquinoline. This was converted to 2-chloro-8-fluoroquinoline by anlogy with Example IV.

Workup

  1. customPrepared
  2. customAfter 30 minutes at 0°-10° the reaction mixture was partitioned between ether and water

Sources & evidence

ORD record
ord-ef646a56d893456c90b9ae60556c14af
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

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