Methanol → HCID 86636844, compound

HRID 420713Notes

Reaction equation

HRID 420713 reaction equation
[Cl:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1.CO>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 58001719HCID 58001719, compound

Product 1

HCID 86636844HCID 86636844, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

CrO2 (Magtrieve) (335 mg, 3.99 mmol) was added to a solution of 3-chloro-5-(hydroxymethyl)-2-pyridinecarbonitrile (33.6 mg, 0.199 mmol) in DCM (2.5 ml) and the mixture was stirred at 40° C. TLC (5% MeOH in DCM) after 3 h showed some starting material. It was heated at 40° C. overnight and full conversion was observed by TLC. The solids were filtered off and the solvent evaporated, yielding 3-chloro-5-formyl-2-pyridinecarbonitrile (19.7 mg, 0.118 mmol, 59% yield) as a white solid.

Workup

  1. temperatureIt was heated at 40° C. overnight
  2. filtrationThe solids were filtered off
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-50c4ee6f39894f7b99ef72de1d7db342
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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