Formaldehyde → HCID 12926025, compound

HRID 894626Notes

Reaction equation

HRID 894626 reaction equation
[N+](C1[C:9]2[O:10][C:11]3([C:14](=[O:15])[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH2:13][CH2:12]3)([O-])=O.C=O.Cl.[CH3:19][N:20]([CH3:22])[CH3:21]>[Ni].C(O)C>[CH3:19][N:20]([CH3:22])[C:21]1[C:9]2[O:10][C:11]3([C:14](=[O:15])[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH2:12][CH2:13]3

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 10313079Trimethylamine HydrochlorideHCID 12925987HCID 12925987, compound

Product 1

HCID 12926025HCID 12926025, compoundYield 138%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-nitrospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (10 g.), formalin (37% formaldehyde, 10 ml.), trimethylamine hydrochloride (2 g.) and Raney nickel (10 g.) in ethanol (500 ml.) was subjected to reduction at 49°-56° C. for 3 hours under hydrogen pressure of 50 kg/cm2. After removing the catalyst by filtration, and the filtrate was concentrated under reduced pressure. The concentrate was dissolved in dichloromethane and the solution was washed with 5% aqueous solution of sodium hydrogen carbonate then with water, followed by drying. The solvent was evaporated off and the residue was subjected to column-chromatography on silica-gel. The first fraction eluted with hexane-ethyl acetate (9:1) was recrystallized from ethanol to give 7-dimethylaminospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (5.87 g.) as yellow needles melting at 68.3° C.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe concentrate was dissolved in dichloromethane
  5. washthe solution was washed with 5% aqueous solution of sodium hydrogen carbonate
  6. customby drying
  7. customThe solvent was evaporated off
  8. washThe first fraction eluted with hexane-ethyl acetate (9:1)
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-e7d89bab0e814171b001958a03a21cc5
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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