Dimethylamine → 3-Dimethylaminomethyl-2-methoxycarbonylindole

HRID 1111378Notes

Reaction equation

HRID 1111378 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[CH3:14][NH:15][CH3:16].[CH2:17]=O>C(O)(=O)C>[CH3:14][N:15]([CH2:17][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4])[CH3:16]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 70992Methyl 1H-indole-2-carboxylate

Product 1

HCID 109114233-Dimethylaminomethyl-2-methoxycarbonylindole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To 51 g ester from (a) was added a mixture of 38 ml dimethylamine, 40 ml acetic acid and 23.5 ml formaldehyde (35% in water). After 20 hours stirring at 80° C. the mixture was cooled and the product isolated by acid-base separation.

Workup

  1. temperaturewas cooled
  2. customthe product isolated by acid-base separation

Sources & evidence

ORD record
ord-3f07e44787614833959c27307d51fde6
Source dataset
uspto-grants-1990_12
Patent number
US04980368

Reaction notes

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