4'-(Bromomethyl)-2-cyanobiphenyl → HCID 18954308, compound

HRID 1491962Notes

Reaction equation

HRID 1491962 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([C:9]1[CH:18]=[C:17]2[C:12]([C:13]([CH3:21])([CH3:20])[CH2:14][C:15](=[O:19])[NH:16]2)=[CH:11][CH:10]=1)[CH3:8].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]#[N:37])=[CH:26][CH:25]=1>CN(C=O)C>[C:36]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:16]2[C:17]3[C:12](=[CH:11][CH:10]=[C:9]([CH2:7][CH3:8])[CH:18]=3)[C:13]([CH3:20])([CH3:21])[CH2:14][C:15]2=[O:19])=[CH:29][CH:28]=1)#[N:37]

Participants

5

Reactant 3

HCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 18954299HCID 18954299, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18954308HCID 18954308, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

12.5 g of potassium tert-butoxide are added at 20° to a solution of 20.3g or 7-ethyl-1,2,3,4-tetrahydro-4,4-dimethyl-2-oxoquinoline [mip. 120°; obtainable by reaction of m-ethylaniline with 3,3-dimethylacryloyl chloride in toluene/methylene chloride to give N-(3,3-dimethylacryloyl)-m-ethylaniline (m.p. 90°) and cyclisation with AlCl3 at 60°-100°]in 700 ml of DMF. The mixure is stirred for 45 minutes, a solution of 30.5g of 4-bromomethyl-2'-cyanobiphenyl in 300 ml of DMF is then added dropwise and the mixture is stirred overnight, evaporated and worked up in conventional manner to give 1-(2'-cyanobiphenyl-4-ylmethyl)-7-ethyl-1,2,3,4-tetrahydro-4,4-dimethyl-2-oxoquinol ine, m.p. 171°-172°.

Workup

  1. stirringthe mixture is stirred overnight
  2. customevaporated

Sources & evidence

ORD record
ord-19e807ac0b1942349d742e2237ffb578
Source dataset
uspto-grants-1994_12
Patent number
US05371226

Reaction notes

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