Sodium Hydroxide → 1-(2,3-dihydro-3-methyl-1H-inden-1-yl)-1H-imidazole-5-carboxylic acid

HRID 5782Notes

Reaction equation

HRID 5782 reaction equation
[N+]([O-])(O)=O.[CH3:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]([N:15]2[C:19]([C:20]([O:22]C)=[O:21])=[CH:18][N:17]=[CH:16]2)[CH2:7]1.[OH-].[Na+]>C(O)(=O)C>[CH3:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]([N:15]2[C:19]([C:20]([OH:22])=[O:21])=[CH:18][N:17]=[CH:16]2)[CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67862033HCID 67862033, compound

Product 1

HCID 197940861-(2,3-dihydro-3-methyl-1H-inden-1-yl)-1H-imidazole-5-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.6 parts of methyl 1-(2,3-dihydro-3-methyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate mononitrate in 50 parts of a sodium hydroxide solution 20% is stirred for 1.5 hours at reflux temperature. After cooling, the reaction mixture is neutralized with acetic acid. The product is extracted with 1,1'-oxybisethane. The extract is dried, filtered and evaporated. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 2.4 parts (90.0%) of 1-(2,3-dihydro-3-methyl-1H-inden-1-yl)-1H-imidazole-5-carboxylic acid; mp. 209.3° C. (compound 2.36).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. extractionThe product is extracted with 1,1'-oxybisethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-a31b6d4ef7e040b1a5ea277dc09e088c
Source dataset
uspto-grants-1993_09
Patent number
US05246915

Reaction notes

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