Hexane → 1-Cyclopropyl-3-cyano-1,4-dihydro-4-oxo-6,7,8-trifluoroquinoline

HRID 1788978Notes

Reaction equation

HRID 1788978 reaction equation
[CH:1]1([NH:4][CH:5]=[C:6]([C:9](=[O:20])[C:10]2[CH:15]=[C:14]([F:16])[C:13]([F:17])=[C:12]([F:18])[C:11]=2F)[C:7]#[N:8])[CH2:3][CH2:2]1.[H-].[Na+].CCCCCC>O1CCOCC1>[CH:1]1([N:4]2[C:15]3[C:10](=[CH:11][C:12]([F:18])=[C:13]([F:17])[C:14]=3[F:16])[C:9](=[O:20])[C:6]([C:7]#[N:8])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8058HexaneHCID 24758Sodium hydrideHCID 867417183-Cyclopropylamino-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile

Product 1

HCID 143023471-Cyclopropyl-3-cyano-1,4-dihydro-4-oxo-6,7,8-trifluoroquinolineYield 91.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-cyclopropylamino-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile (12.0 g) in dioxane (60 ml) is added dropwise to a suspension of sodium hydride (1.9 g, in oil, 55-65 w/w%) in dioxane (40 ml) while maitainig the internal temperature between 16° C. and 18° C. on an ice bath. The mixture is stirred for 6 hours with heating while keeping the internal temperature around 45° C. The reaction mixture is poured into hexane (300 ml), and the resulting precipitate is filtered and washed with hexane and water to yield 1-cyclopropyl-3-cyano-1,4-dihydro-4-oxo-6,7,8-trifluoroquinoline (10.2 g) as a colorless powder, m.p. 217°-218° C.

Workup

  1. customthe internal temperature between 16° C. and 18° C.
  2. temperaturewith heating
  3. customthe internal temperature around 45° C
  4. filtrationthe resulting precipitate is filtered
  5. washwashed with hexane and water

Sources & evidence

ORD record
ord-bb4faac45a8f4f5d8929cdcc7278d10a
Source dataset
uspto-grants-1987_08
Patent number
US04686221

Reaction notes

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