Dimethyl Sulfate → Ethyl 3-methyl-3H-naphtho[2,3-e]indole-2-carboxylate

HRID 359233Notes

Reaction equation

HRID 359233 reaction equation
S(OC)(O[CH3:5])(=O)=O.[CH:8]1[C:16]2[C:15]3[CH:17]=[C:18]4[C:23](=[CH:24][C:14]=3[CH:13]=[CH:12][C:11]=2[NH:10][C:9]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19]4>CCOC(C)=O.CCCCCC>[CH3:5][N:10]1[C:11]2[CH:12]=[CH:13][C:14]3[CH:24]=[C:23]4[C:18](=[CH:17][C:15]=3[C:16]=2[CH:8]=[C:9]1[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:19]=[CH:20][CH:21]=[CH:22]4

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 20065895HCID 20065895, compound

Product 1

HCID 20065894Ethyl 3-methyl-3H-naphtho[2,3-e]indole-2-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using the procedure described in Example 34A except that dimethyl sulfate was used as the alkylating agent, ethyl 3H-naphth[2,3-e]indole-2-carboxylate (H.G. Pars Pharmaceutical Laboratories, Inc.) gave a 97% yield of ethyl 3-methyl-3H-naphth[2,3-e]indole-2-carboxylate, mp 141°-144°, (EtOAc/hexane), (C,H,N).

Sources & evidence

ORD record
ord-2663904bb0504f58a8dace3bbcfadf94
Source dataset
uspto-grants-1991_03
Patent number
US04999369

Reaction notes

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