Formaldehyde → HCID 21270045, compound

HRID 1194347Notes

Reaction equation

HRID 1194347 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=[O:13])[CH3:12])=[C:3]1[CH3:14].[CH2:15]=O.Cl.[CH3:18][NH:19][CH3:20]>C(O)C>[CH3:18][N:19]([CH3:15])[CH2:20][CH2:12][C:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]=1[CH3:14])=[O:13]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 2857551-(1,2-dimethyl-1H-indol-3-yl)ethanone

Product 1

HCID 21270045HCID 21270045, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(1,2-dimethyl-1H-indol-3-yl)-1-ethanone (0.9 g), paraformaldehyde (0.43 g) and dimethylamine hydrochloride (1.2 g) in ethanol (60 ml) was heated at reflux for 18 h, cooled, and the solvent evaporated in vacuo. The residue was partitioned between sodium carbonate (2N; 50 ml) and ethyl acetate (2×50 ml) and the combined organic extracts were dried and evaporated in vacuo to give an oil. This oil was chromatographed eluting with System A to give the title compound, which on standing gave crystals (0.9 g), m.p. 96°-98°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. customthe solvent evaporated in vacuo
  5. customThe residue was partitioned between sodium carbonate (2N; 50 ml) and ethyl acetate (2×50 ml)
  6. customthe combined organic extracts were dried
  7. customevaporated in vacuo
  8. customto give an oil
  9. customThis oil was chromatographed
  10. washeluting with System A

Sources & evidence

ORD record
ord-e02d5304419841458093e9e28ad2f016
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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