HCID 18412373, compound → HCID 18412360, compound

HRID 2288332Notes

Reaction equation

HRID 2288332 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-hydroxymethyl-imidazo[4,5-b]pyridine were dissolved in 500 ml dichloromethane and mixed with 15.0 g of manganese dioxide. After 96 hours at room temperature the mixture was filtered through kieselgur 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: 231-234° C.

Workup

  1. filtrationAfter 96 hours at room temperature the mixture was filtered through kieselgur
  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-27c0bf1d1ecd411eb5d7bcb695a47933
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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