2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 178479880, compound

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12](=[O:19])[CH:13]=[C:14]([C:16](O)=[O:17])[O:15][C:5]=3[C:4]=2[CH:3]=1.C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C.O.[NH2:39][C:40]1[NH:44][N:43]=[N:42][N:41]=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12](=[O:19])[CH:13]=[C:14]([C:16]([NH:39][C:40]4[NH:44][N:43]=[N:42][N:41]=4)=[O:17])[O:15][C:5]=3[C:4]=2[CH:3]=1

Participants

Procedure

A mixture of 2.5 g (9.1 mmole) 8-chloro-4, 5-dihydro-5-methyl-4-oxopyrano[3,2-b]indole-2-carboxylic acid and 4.8 g (19.7 mmole) N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ) in 300 ml benzene was stirred for 45 min under nitrogen. To the reaction mixture was added 1.1 g (10.7 mmole) of 5-aminotetrazole monohydrate, and stirring was continued for a total of 88 hrs. The precipitate that had formed was filtered, stirred overnight in 50 ml of methanol, and refiltered. Two recrystallizations from DMF yielded a yellow solid of mp 300° C. dec.