Acetic Acid → Indole, 5-bromo-3-(dimethylamino)methyl-

HRID 224895

Reaction equation

HRID 224895 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C=O.[CH3:13][NH:14][CH3:15].[C:16](O)(=O)C>O1CCOCC1>[CH3:13][N:14]([CH2:16][C:5]1[C:4]2[CH:3]=[C:2]([Br:1])[CH:10]=[CH:9][C:8]=2[NH:7][CH:6]=1)[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 249055-Bromoindole

Product 1

HCID 13249Indole, 5-bromo-3-(dimethylamino)methyl-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

This material was prepared by the method of Procedure 67B from 49.5 g. of 5-bromoindole, 20 ml. of 37% aqueous formaldehyde, 55 ml. of 25% aqueous dimethylamine, 250 ml. of acetic acid and 250 ml. of dioxane; yield 60.6 g., m.p. 154°-156° C. The structure was confirmed by examination of the NMR spectrum.

Workup

  1. customThis material was prepared by the method of Procedure 67B from 49.5 g

Sources & evidence

ORD record
ord-b8d02287528a42eeb37d82ed1423ce24
Source dataset
uspto-grants-1980_11
Patent number
US04234595

Linked notes

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