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

HRID 359232Notes

Reaction equation

HRID 359232 reaction equation
S(OC)(O[CH3:5])(=O)=O.[CH:8]1[C:16]2[CH:15]=[CH:14][C:13]3[C:17]4[C:22]([CH:23]=[CH:24][C:12]=3[C:11]=2[NH:10][C:9]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=[CH:19][CH:18]=4>C(Cl)Cl.CCCCCC>[CH3:5][N:10]1[C:11]2[C:12]3[CH:24]=[CH:23][C:22]4[C:17]([C:13]=3[CH:14]=[CH:15][C:16]=2[CH:8]=[C:9]1[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:18][CH:19]=[CH:20][CH:21]=4

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 20065898ethyl 3H-naphth[1,2-g]indole-2-carboxylate

Product 1

HCID 20065897ethyl 3-methyl-3H-naphth[1,2-g]indol-2-carboxylateYield 74.5%

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 3H-naphth[1,2-g]indole-2-carboxylate (H. G. Pars Pharmaceutical Laboratories, Inc.) gave a 74.5% yield of ethyl 3-methyl-3H-naphth[1,2-g]indol-2-carboxylate, mp 136°-138°, (CH2Cl2 /hexane), (C,H,N).

Sources & evidence

ORD record
ord-6a6e8c822d2b46d0a8219c1640d82ff5
Source dataset
uspto-grants-1991_03
Patent number
US04999369

Reaction notes

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