Potassium Hydroxide → 4-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-1H-pyridin-2-one

HRID 2194383

Reaction equation

HRID 2194383 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[C:11]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[N:10]=[C:9]2[CH3:22])[CH:5]=[CH:4][N:3]=1.[OH-:23].[K+]>C(O)(C)(C)C>[Cl:21][C:17]1[CH:16]=[C:15]([C:14]#[C:13][C:11]2[N:10]=[C:9]([CH3:22])[N:8]([C:6]3[CH:5]=[CH:4][NH:3][C:2](=[O:23])[CH:7]=3)[CH:12]=2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 866498792-Chloro-4-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-pyridine

Product 1

HCID 498725744-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-1H-pyridin-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-chloro-4-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-pyridine (120 mg, 0.366 mmol) was dissolved in 6 ml tert-butanol. A 50% solution of KOH (2 ml, 26.7 mmol) was added and the mixture was refluxed for 72 h. The reaction mixture was concentrated in vaccuo, the pH was adjusted to 7 by addition of 37% HCl solution, and the aqueous phase was extracted twice with 40 ml of ethyl acetate. The organic phase was washed once with 10 of brine, dried with magnesium sulfate, filtered and evaporated. The title compound (104 mg, 0.336 mmol, 92%) was obtained as a crystalline light yellow solid, MS: m/e=310.1, 312.2 (M+H+).

Workup

  1. temperaturethe mixture was refluxed for 72 h
  2. concentrationThe reaction mixture was concentrated in vaccuo
  3. additionthe pH was adjusted to 7 by addition of 37% HCl solution
  4. extractionthe aqueous phase was extracted twice with 40 ml of ethyl acetate
  5. washThe organic phase was washed once with 10 of brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-33a9a3ece6064042821a696eb2f189cf
Source dataset
uspto-grants-2012_12
Patent number
US08334287B2

Linked notes

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