HCID 303251, compound → 6-Fluoro-1,2-dihydroquinolin-2-one

HRID 1772201Notes

Reaction equation

HRID 1772201 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[CH:10]=[CH:11]C2C=CC=CC=2)=[CH:4][CH:3]=1.[Cl-:19].[Cl-].[Cl-].[Al+3]>>[ClH:19].[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][C:9](=[O:18])[CH:10]=[CH:11]2

Participants

4

Reactant 2

HCID 303251HCID 303251, compoundHCID 6451240Aluminum(III) Chloride

Product 2

HCID 313Hydrochloric AcidYield 5%HCID 98340436-Fluoro-1,2-dihydroquinolin-2-oneYield 113.8%

Conditions

Temperature
100 °C

Procedure

An intimate mixture of N-(4-fluorophenyl)cinnamamide (10 g, 42 mmol) and aluminum trichloride (16.4 g, 123 mmol, 3 eq) was heated rapidly to melting and then heated at 100° C. for 3 h. After cooling to room temperature, ice-water was added and the resultant precipitate was washed with water (300 ml) and then with 5% aqueous hydrochloric acid (3×100 ml) to afford 6-fluoro-1,2-dihydroquinolin-2-one as a brown solid (7.8 g, 88%) which was used without further purification; (ES, m/z): [M+H]+ 164; 1H NMR (300 MHz, DMSO): δ 11.82 (broad s, 1H), 7.86 (d, J=9.4 Hz, 1H), 7.61 (d, J=8.7 Hz, 1H), 7.29-7.40 (m, 2H), 6.54 (d, J=9.4 Hz, 1H).

Workup

  1. temperaturewas heated rapidly
  2. temperatureAfter cooling to room temperature
  3. washthe resultant precipitate was washed with water (300 ml)

Sources & evidence

ORD record
ord-25188eb0e8f449f69897c73ae8555fe9
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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