HCID 18412373, compound → HCID 18412360, compound

HRID 50201Notes

Reaction equation

HRID 50201 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([CH2:11][OH:12])=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 18412373HCID 18412373, compound

Product 1

HCID 18412360HCID 18412360, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

3.65 g (12.5 mmol) of 1-methyl-2-[(4-cyanophenyl)oxymethyl]-5-hydroxymethylimidazo[4,5-b]pyridine were dissolved in 500 mL of dichloromethane and mixed with 15.0 g of manganese dioxide. After 96 hours at room temperature, the mixture was filtered through kieselguhr and the solvent was distilled off. The filtrate obtained was evaporated down, the crystalline precipitate was triturated with ether, suction filtered, and dried. Yield: 3.05 g white powder (84% of theory), C16H12N4O2 (292.30); melting point: 231° C.-234° C.

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. distillationthe solvent was distilled off
  3. customThe filtrate obtained
  4. customwas evaporated down
  5. customthe crystalline precipitate was triturated with ether, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-3b55e0289f314cf88ad1af857b563a3f
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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