Methyl iodide → HCID 21552248, compound

HRID 268461Notes

Reaction equation

HRID 268461 reaction equation
[CH3:1][C:2]([N+:17]([O-:19])=[O:18])([CH2:15][CH3:16])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][CH:5]=1.[H-].[Na+].[CH3:22]I>CN(C)P(=O)(N(C)C)N(C)C>[CH3:22][N:6]1[C:7]2[C:12](=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[C:4]([CH2:3][C:2]([CH3:1])([N+:17]([O-:19])=[O:18])[CH2:15][CH3:16])=[CH:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21552259HCID 21552259, compound

Product 1

HCID 21552248HCID 21552248, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

If the 3-(2'-methyl-2'-nitrobutyl)-5-methoxy-indole obtained as intermediate product in Example 2 is methylated by the procedure described in Example 4 (or by means of sodium hydride and methyl iodide in hexamethyl phosphoric acid triamide), 1-methyl-3-(2'-methyl-2'-nitrobutyl)-5-methoxy-indole is obtained and melts at 95°-96°C. after crystallisation from acetone/water and distillation. Catalytic reduction thereof yields 1-methyl-3-(2'-methyl-2'-aminobutyl)-5-methoxy-indole. Melting point of the benzoic acid salt 179.5°-184°C. (insoluble in ether).

Sources & evidence

ORD record
ord-8fb34a85a61c4c2781aa6f678718e8bf
Source dataset
uspto-grants-1976_03
Patent number
US03947584

Reaction notes

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