Diketene → HCID 19864538, compound

HRID 1199987Notes

Reaction equation

HRID 1199987 reaction equation
[CH3:1][C:2]1[N:3]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[CH2:16]=[C:17]1[O:21][C:19](=[O:20])[CH2:18]1>CC(C)=O>[O:21]=[C:17]([CH3:16])[CH2:18][C:19]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][N:3]1[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=[C:2]1[CH3:1])=[O:20]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 19864515HCID 19864515, compound

Product 1

HCID 19864538HCID 19864538, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-methyl-1-(4-hydroxybutyl)imidazo[4,5-c]pyridine (0.5 g) in acetone (10 ml) at room temperature was added, dropwise, freshly distilled diketene (0.2 g). The solution was stirred at room temperature for 2 hours and then evaporated to dryness. The residue was chromatographed on silica gel eluting with a methylene chloride-ethyl acetate mixture and the fractions containing the product were evaporated under vacuum to leave the title compound, (0.51 g).

Workup

  1. customevaporated to dryness
  2. customThe residue was chromatographed on silica gel eluting with a methylene chloride-ethyl acetate mixture
  3. additionthe fractions containing the product
  4. customwere evaporated under vacuum

Sources & evidence

ORD record
ord-0450cf5e75024996b40d36eea57e1785
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

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