1,3-Dichloroacetone → 2-(Chloromethyl)imidazo[1,2-a]pyridine-7-carbonitrile hydrochloride

HRID 908254Notes

Reaction equation

HRID 908254 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[Cl:10][CH2:11][C:12]([CH2:14]Cl)=O>C(O)C>[ClH:10].[Cl:10][CH2:11][C:12]1[N:1]=[C:2]2[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][N:9]2[CH:14]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 70155242-Aminoisonicotinonitrile

Product 1

HCID 671323142-(Chloromethyl)imidazo[1,2-a]pyridine-7-carbonitrile hydrochlorideYield 115.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol 50 mL solution of 2-amino-isonicotinonitrile (5.0 g, 42 mmol) was added 1,3-dichloroacetone (6.93 g, 54.6 mmol). The mixture was heated to reflux for 1.5 hr and cooled to room temperature to give a suspension. The precipitate was collected by suction filtration, washed with dichloromethane and dried to give the title compound (7.2 g). LC/MS: m/z 192(M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hr
  3. customto give a suspension
  4. filtrationThe precipitate was collected by suction filtration
  5. washwashed with dichloromethane
  6. customdried

Sources & evidence

ORD record
ord-026cd9b7fce84a00b93ec4eb504972d8
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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