Dimethyl Sulfate → ethyl 1-methyl-1H-naphth[2,3-g]indole-2-carboxylate

HRID 359234Notes

Reaction equation

HRID 359234 reaction equation
S(OC)(O[CH3:5])(=O)=O.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]3[CH:24]=[C:23]4[C:18]([CH:19]=[CH:20][CH:21]=[CH:22]4)=[CH:17][C:15]3=2)[CH:10]=[C:9]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(Cl)Cl.CCCCCC>[CH3:5][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]3[CH:24]=[C:23]4[C:18]([CH:19]=[CH:20][CH:21]=[CH:22]4)=[CH:17][C:15]3=2)[CH:10]=[C:9]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 20065844ethyl 1H-naphth[2,3-g]indole-2-carboxylate

Product 1

HCID 20065877ethyl 1-methyl-1H-naphth[2,3-g]indole-2-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

Using the procedure outlined in Example 34A except that dimethyl sulfate was used as the alkylating agent, ethyl 1H-naphth[2,3-g]indole-2-carboxylate (H.G. Pars Pharmaceutical Laboratories, Inc.) gave a 96.2% yield of ethyl 1-methyl-1H-naphth[2,3-g]indole-2-carboxylate, mp 165°-165.5°, (CH2Cl2 /hexane), (C,H,N).

Sources & evidence

ORD record
ord-5a0c7cd76e8745c5a884f1b4b6a8b5b3
Source dataset
uspto-grants-1991_03
Patent number
US04999369

Reaction notes

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