Imidazole → 5-(1H-imidazol-1-yl)-2-methyl-1-indanone

HRID 1723317Notes

Reaction equation

HRID 1723317 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([CH3:12])[CH2:5]2.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>C(OCC)(=O)C>[N:13]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH:6]([CH3:12])[CH2:5]3)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 30162575-Fluoro-2-methylindan-1-one

Product 1

HCID 200255615-(1H-imidazol-1-yl)-2-methyl-1-indanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
175 °C

Procedure

A stirred melt of 5-fluoro-2-methyl-1-indanone (4.9 g) and imidazole (9.8 g) was heated under nitrogen at 175° C. for 2 hours. The warm melt was diluted with ethyl acetate (100 ml), the resulting solution extracted with dilute hydrochloric acid, and the acidic extract treated with potassium carbonate to pH 6. Extraction of the mixture with ethyl acetate with dichloromethane failed to dissolve all of the solids and the mixture was filtered to remove a solid by-product, 5-(1H-imidazol-1-yl)-2-methyl-1H-inden-1-one, 0.92 g, m.p. 215°-217° C. (from toluene). The combined aqueous and organic solutions were evaporated to leave an aqueous mixture which deposited a sticky solid; further product was obtained by ethyl acetate extraction. The combined crude product (5.36 g) was purified by medium pressure column chromatography (silica gel, chloroform) to give 5-(1H-imidazol-1-yl)-2-methyl-1-indanone, 3 g (47%), m.p. 103°-106° C., which was used directly in the next stage.

Workup

  1. extractionthe resulting solution extracted with dilute hydrochloric acid
  2. extractionthe acidic extract
  3. additiontreated with potassium carbonate to pH 6
  4. extractionExtraction of the mixture with ethyl acetate with dichloromethane
  5. dissolutionto dissolve all of the solids
  6. filtrationthe mixture was filtered
  7. customto remove a solid by-product, 5-(1H-imidazol-1-yl)-2-methyl-1H-inden-1-one, 0.92 g, m.p. 215°-217° C. (from toluene)
  8. customThe combined aqueous and organic solutions were evaporated
  9. customto leave an aqueous mixture which
  10. customwas purified by medium pressure column chromatography (silica gel, chloroform)

Sources & evidence

ORD record
ord-1b1da5c974744390ab867b7253aecc6e
Source dataset
uspto-grants-1989_08
Patent number
US04861773

Reaction notes

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