Oxalic Acid → HCID 12925996, compound

HRID 894617Notes

Reaction equation

HRID 894617 reaction equation
[N+:1]([C:4]1[CH:15]=[C:14]([N+:16]([O-])=O)[C:7]2[O:8][C:9]3([C:12](=[O:13])[C:6]=2[CH:5]=1)[CH2:11][CH2:10]3)([O-])=O.[H][H].C(O)(=O)C(O)=O>[Pt](=O)=O.C(O)C>[NH2:1][C:4]1[CH:15]=[C:14]([NH2:16])[C:7]2[O:8][C:9]3([C:12](=[O:13])[C:6]=2[CH:5]=1)[CH2:11][CH2:10]3

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 12925988HCID 12925988, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12925996HCID 12925996, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

250 mg. of 5,7-Dinitrospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one, 50 mg. of platinum dioxide and 20 ml. of ethanol were stirred in a stream of hydrogen for 1.25 hour under atmospheric pressure. To the reaction mixture was added oxalic acid, and the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure until its volume became above 3 ml. Ether was added to the concentrate, and the resulting powder was collected by filtration. The powder was dissolved in ethanol. To the ethanolic solution was added activated charcoal for decoloration, followed by addition of ether. The precipitating powder was collected by filtration to obtain 5,7-diaminospiro[benzo[b]furan-2(3H),1'-cyclopropane]3-one.1/2 oxalate.monohydrate as yellowish brown powder.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure until its volume
  3. additionEther was added to the concentrate
  4. filtrationthe resulting powder was collected by filtration
  5. dissolutionThe powder was dissolved in ethanol
  6. additionTo the ethanolic solution was added
  7. additionfollowed by addition of ether
  8. filtrationThe precipitating powder was collected by filtration

Sources & evidence

ORD record
ord-f7b6e43d291e490f88c9522753ecd6ce
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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