Sodium hydride → HCID 19864365, compound

HRID 1199933Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:13]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](OC)=[C:24]([C:27]#[N:28])[C:25]#[N:26])=[CH:19][CH:18]=1)(=[O:15])[CH3:14].[H-].[Na+]>CN(C)C=O>[C:13]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:2]3[N:1]([C:27](=[NH:28])[C:24]=2[C:25]#[N:26])[CH:6]=[CH:5][CH:4]=[CH:3]3)=[CH:19][CH:18]=1)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 165 mg of ethyl 2-pyridylacetate and 242 mg of 3-(4-acetoxyphenyl)-2-cyano-3-methoxyacrylonitrile was dissolved in 1 ml of dry N,N-dimethylformamide. To the solution was added 40 mg of 60% sodium hydride at room temperature and the reaction mixture was stirred for 1 hour at 60° C. The reaction mixture was poured into ice-water, and precipitated crystals were collected by filtration, washed with water and dried to obtain 120 mg of 2-(4-acetoxyphenyl)-3-cyano-1-ethoxycarbonyl-4-imino-4H-quinolizin. The obtained imine compound was added to 5 ml of 90% acetic acid and the reaction mixture was heated under reflux for 72 hours. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane, and the solution was washed successively with 1N-hydrochloric acid, water and saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was recrystallized from methanol to obtain 75 mg of 3-cyano-1-ethoxycarbonyl-2-(4-hydroxyphenyl)-4H-quinolizin-4-one.

Workup

customprecipitated crystals
filtrationwere collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-e0ba0b4506ff422b8a7200afe9df0240
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04904657

Reaction notes

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