Benzoyl chloride → 1-Benzoyl-6-chloro-1,2-dihydroquinoline-2-carbonitrile

HRID 1585573Notes

Reaction equation

HRID 1585573 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[Si]([C:25]#[N:26])(C)C>C(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>[C:12]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]1[C:25]#[N:26])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 691636-ChloroquinolineHCID 82115Trimethylsilyl cyanide

Product 1

HCID 133367791-Benzoyl-6-chloro-1,2-dihydroquinoline-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-chloroquinoline (9.5 g), benzoyl chloride (13.2 g) in methylene chloride (50 mL) was treated with AlCl3 (0.10 g) followed by dropwise addition of trimethyl silyl cyanide (12.5 mL). After 0.5 hour, the mixture was diluted with 150 mL of methylene chloride and washed with water, 1N HCl, saturated sodium bicarbonate (aq.), and brine. The organic phase was dried over magnesium sulfate then evaporated to dryness. The residue was purified by column chromatography on silica gel using ethyl acetate/hexane (3:7) as the eluting solvent. The title compound (13 g) was obtained as a white solid, m.p. 141-143° C. This product was used for the preparation of the title compound described in step 2.

Workup

  1. washwashed with water, 1N HCl, saturated sodium bicarbonate (aq.), and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthen evaporated to dryness
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b28014d7ac24484e83c9b1f972a3472e
Source dataset
uspto-grants-1999_08
Patent number
US05939435

Reaction notes

Loading…