Dimethylamine → HCID 10823474, compound

HRID 327080Notes

Reaction equation

HRID 327080 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[CH3:14][NH:15][CH3:16].[CH2:17]=O.[OH-].[Na+]>C(O)(=O)C>[CH3:14][N:15]([CH2:17][C:3]1[C:4]2[C:5]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=[CH:8][C:9]=2[NH:1][CH:2]=1)[CH3:16]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 10823474HCID 10823474, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

100 g of methyl indole-4-carboxylate were dissolved in 500 ml of glacial acetic acid. To the solution were added dropwise at room temperature a mixture of 86 ml of a 40% strength aqueous dimethylamine solution, 55 ml of a 37% strength aqueous formaldehyde solution and 250 ml of glacial acetic acid. The reaction mixture was subsequently stirred at room temperature for 20 hours. To work up the reaction mixture it was cooled in ice and 20% strength aqueous sodium hydroxide solution was added until pH 9 was reached. This was followed by extraction three times with dichloromethane, and the combined organic extracts were dried with sodium sulfate, filtered and concentrated. 127 g of crude methyl 3-dimethylaminomethylindole-4-carboxylate were obtained as a pale yellow oil.

Workup

  1. additionTo the solution were added dropwise at room temperature
  2. temperaturewas cooled in ice
  3. extractionThis was followed by extraction three times with dichloromethane
  4. dry with materialthe combined organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1abc8945d25a430ca0e9b0928fb26dc9
Source dataset
uspto-grants-1993_12
Patent number
US05272143

Reaction notes

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