Methyl iodide → 6,11-Dihydro-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

HRID 1862968Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][C:6]=2[N:17]=1.[H-].[Na+].[CH3:20]I>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[N:10]([CH3:20])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][C:6]=2[N:17]=1

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture consisting of 11.3 gm (0.05 mol) of 6,11-dihydro-2-methyl-5H-pyrido[2,3-b][1,5]-benzodiazepin-5-one (prepared according to C.A. 74, 53868y, 1971), 150 ml of dimethyl formamide, and 2.8 gm of 50% sodium hydride in mineral oil was stirred at 30° C. in a nitrogen atmosphere for 1 hour. Then, a solution of 10.7 gm (0.075 mol) of methyl iodide in 30 ml of dimethyl formamide was added dropwise while stirring, and the mixture was heated on an oil bath at 100° C. for 3 hours while stirring and then evaporated in vacuo, and an aqueous sodium carbonate solution was stirred into the residue. The mixture was suction-filtered, and the filter cake was washed with water and recrystallized from xylene, yielding 80% of theory of the compound named in the heading, which had a melting point of 192°-194° C.

Workup

stirringwhile stirring
temperaturethe mixture was heated on an oil bath at 100° C. for 3 hours
stirringwhile stirring
customevaporated in vacuo
stirringan aqueous sodium carbonate solution was stirred into the residue
filtrationThe mixture was suction-filtered
washthe filter cake was washed with water
customrecrystallized from xylene
customyielding 80% of theory of the compound

Sources & evidence

ORD record: ord-be5c2945e59a4836a98f2194343cb10f
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04167570

Reaction notes

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