Oxalic Acid → HCID 13487085, compound

HRID 648008Notes

Reaction equation

HRID 648008 reaction equation
C([C:9]1[CH:10]=[C:11]2[CH:17]([C:18]([O:20]C)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[CH:22]=1)(=O)C1C=CC=CC=1.[C:23](=[O:26])([O-])[O-].[K+].[K+].[C:29](O)(=O)[C:30](O)=O>CO.O>[C:23]([C:22]1[N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([C:18]([OH:20])=[O:19])[C:11]2=[CH:10][CH:9]=1)(=[O:26])[C:30]1[CH:29]=[CH:11][CH:10]=[CH:9][CH:22]=1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 11430Potassium CarbonateHCID 20484249HCID 20484249, compound

Product 1

HCID 13487085HCID 13487085, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 2-benzoyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine-9-carboxylate (1.00 g., 0.0034 moles) in methanol (30 ml.) and water (10 ml.) containing potassium carbonate (0.940 g., 0.0068 moles) was heated at reflux temperature, in a nitrogen atmosphere, for 2 hours. The solvent was removed in vacuo, water (25 ml.) was added and the solution was extracted with ether (2×50 ml.). The aqueous phase was cooled to 5°, oxalic acid (2.55 g., 0.02 moles) was added, and after agitation for 0.5 hours the product was extracted into ethyl acetate (3×100 ml.). The extract was washed with water, dried over sodium sulfate and evaporated in vacuo. The residue, on crystallization from ethylacetate/hexane gives 3-benzoyl-5,6,7,8-tetrahydro-9H-pyrrolo[1,2-a]azepine-9-carboxylic acid in 73% yield, m.p. 163°-165° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature
  3. customThe solvent was removed in vacuo, water (25 ml.)
  4. additionwas added
  5. extractionthe solution was extracted with ether (2×50 ml.)
  6. temperatureThe aqueous phase was cooled to 5°
  7. extractionafter agitation for 0.5 hours the product was extracted into ethyl acetate (3×100 ml.)
  8. washThe extract was washed with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated in vacuo
  11. customThe residue, on crystallization from ethylacetate/hexane

Sources & evidence

ORD record
ord-d933fca3908a47beb8d8cd7b2a1b6a69
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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