m,alpha-Dichlorotoluene → Ethyl 9-(3-chlorobenzyl)-6-nitro-9H-beta-carboline-3-carboxylate

HRID 891020Notes

Reaction equation

HRID 891020 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1[CH:11]=[N:10][C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][C:7]2=1)([O-:3])=[O:2].[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Cl>>[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][N:13]1[C:12]2[CH:11]=[N:10][C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][C:7]=2[C:6]2[C:14]1=[CH:15][CH:16]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2

Participants

3

Reactant 2

HCID 12103m,alpha-DichlorotolueneHCID 13037332ethyl 6-nitro-9H-beta-carboline-3-carboxylate

Product 1

HCID 21883399Ethyl 9-(3-chlorobenzyl)-6-nitro-9H-beta-carboline-3-carboxylate

Procedure

The title compound was prepared by alkylation of ethyl 6-nitro-9H-β-carboline-3-carboxylate (prepared according to Settimj, et. al., J. Heterocycl. Chem., 25, 1391–1397 (1988)) with 3-chlorobenzyl chloride in a manner similar to step (a) of example 7. LCMS (APCI, M+H+): 410.1/412.1=3/1.

Sources & evidence

ORD record
ord-d20e1727ac2045d59427c10924672668
Source dataset
uspto-grants-2006_02
Patent number
US07001912B2

Reaction notes

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