Formaldehyde → HCID 11161534, compound

HRID 893318Notes

Reaction equation

HRID 893318 reaction equation
[C:1]1([CH:7]([NH2:19])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]=O>CO>[CH3:18][O:17][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][C:12]=1[O:15][CH3:16])[CH2:20][NH:19][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:8]2

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 411721HCID 411721, compound

Product 1

HCID 11161534HCID 11161534, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Heat a mixture of the amine from step C, 36% formaldehyde (1 mL) and 1.5 mL of methanol at reflux for 2 h. Distill off the solvent, add 3 mL of benzene to the residue and concentrate in vacuo to a residue. Add 3 mL of benzene and again concentrate to a residue. Add 2 mL of methanolic HCl (1.5N) and heat the mixture at reflux for 2 h. Pour the mixture into water, neutralize with NH4OH and extract with ethyl acetate. Concentrate the extract to give 286 mg of the title compound. 1H NMR (CDCl3): δ7.53-7.23 (5H, m); 6.6 (2H, d, J=2 Hz); 4.3-3.72 (3H, m); 3.87 (3H, s); 3.85 (3H, s); 2.9 (2H, d, J=7 Hz).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 2 h
  3. distillationDistill off the solvent
  4. additionadd 3 mL of benzene to the residue
  5. concentrationconcentrate in vacuo to a residue
  6. additionAdd 3 mL of benzene
  7. concentrationagain concentrate to a residue
  8. additionAdd 2 mL of methanolic HCl (1.5N)
  9. temperatureheat the mixture
  10. temperatureat reflux for 2 h
  11. additionPour the mixture into water
  12. extractionextract with ethyl acetate
  13. concentrationConcentrate the
  14. extractionextract

Sources & evidence

ORD record
ord-c3acbefdb20d40e1bd06f87deb867e43
Source dataset
uspto-grants-1992_06
Patent number
US05124337

Reaction notes

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