HCID 58001743, compound → HCID 58001780, compound

HRID 420743Notes

Reaction equation

HRID 420743 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([OH:13])([CH3:12])[CH3:11])=[N:4][CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[N:4][C:3]=1[C:10]([OH:13])([CH3:12])[CH3:11]

Participants

3

Reactant 1

HCID 58001743HCID 58001743, compound

Product 1

HCID 58001780HCID 58001780, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

CrO2 (Magtrieve) (1749 mg, 20.83 mmol) was added to a solution of 2-[3-chloro-5-(hydroxymethyl)-2-pyridinyl]-2-propanol (210 mg, 1.041 mmol) in DCM (10 mL) and the mixture was stirred at 40° C. overnight. The suspension was filtered over nylon membrane and it was rinsed with DCM. The process was repeated several times. The combined filtrates were concentrated to afford 5-chloro-6-(1-hydroxy-1-methylethyl)-3-pyridinecarbaldehyde (179 mg, 82%) as yellow solid. It was used in the next step without further purification.

Workup

  1. filtrationThe suspension was filtered over nylon membrane and it
  2. washwas rinsed with DCM
  3. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-738239666e9a49da8ed61c4967f73263
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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