Chloroacetonitrile → cyanomethyl 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylate

HRID 1583404Notes

Reaction equation

HRID 1583404 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]1[CH:14]=[CH:15][C:16]([C:18]([OH:20])=[O:19])=[CH:17][N:8]1[C:7]2=[O:21])[CH3:3].Cl[CH2:23][C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:24]([CH2:23][O:19][C:18]([C:16]1[CH:15]=[CH:14][C:9]2[N:8]([CH:17]=1)[C:7](=[O:21])[C:6]1[C:11](=[CH:12][CH:13]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=1)[N:10]=2)=[O:20])#[N:25]

Participants

6

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 12562128HCID 12562128, compound

Product 1

HCID 13557516cyanomethyl 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 20 g of 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid, 6.3 ml of chloroacetonitrile and 13.2 g of potassium carbonate in 100 ml of dimethylformamide was stirred 18 hours at room temperature. The reaction mixture was diluted with 200 ml of water and the precipitated product collected to give 21.63 g (95%) of 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid cyanomethyl ester, mp 186°-188° C.

Workup

  1. customthe precipitated product collected

Sources & evidence

ORD record
ord-e073f121c242424384694051a3deb4e2
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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