Dimethylformamide → 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid 3-(3-pyridyl)propyl ester

HRID 1583392Notes

Reaction equation

HRID 1583392 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].C(=O)([O-])[O-].[K+].[K+].[CH3:28][N:29]([CH3:32])C=O>>[N:29]1[CH:32]=[CH:1][CH:2]=[C:4]([CH2:13][CH2:12][CH2:11][O:19][C:18]([C:16]2[CH:15]=[CH:14][C:9]3[N:8]([CH:17]=2)[C:7](=[O:21])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=2)[N:10]=3)=[O:20])[CH:28]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12562128HCID 12562128, compound

Product 1

HCID 135574912-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid 3-(3-pyridyl)propyl esterYield 38%

Conditions

Temperature
70 °C

Procedure

A mixture of 5.0 g of 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid, 5.2 g of 3-(3-pyridine)propylbromide hydrobromide, and 5.2 g of potassium carbonate in 200 ml of dimethylformamide was heated to a bath temperature of 70° C. for 45 minutes. The reaction mixture was partitioned between water (100 ml) and dichloromethane (100 ml) and the aqueous layer was extracted with 3×100 ml of dichloromethane. The combined extracts were washed with 100 ml portions of 10% sodium hydroxide and water, were dried over potassium carbonate and evaporated to 6.3 g of an oil which was purified by preparative liquid chromatography over silica gel eluting with 3:1 ethyl acetate-hexane. The major fraction contained 4.6 g of a orange oil which was crystallized from ethyl acetate-hexane to give 2.7 g (38%) of 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid 3-(3-pyridyl)propyl ester, mp 108°-109° C.

Workup

  1. customThe reaction mixture was partitioned between water (100 ml) and dichloromethane (100 ml)
  2. extractionthe aqueous layer was extracted with 3×100 ml of dichloromethane
  3. washThe combined extracts were washed with 100 ml portions of 10% sodium hydroxide and water
  4. dry with materialwere dried over potassium carbonate
  5. customevaporated to 6.3 g of an oil which
  6. customwas purified by preparative liquid chromatography over silica gel eluting with 3:1 ethyl acetate-hexane
  7. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2caa1fad687b488daef059af265ee1ca
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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