Methanol → HCID 178431769, compound

HRID 1655240Notes

Reaction equation

HRID 1655240 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][N+:5]([O-])=[C:4](C)[CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CO.[C:26]([O-:29])([O-])=O.[K+].[K+]>ClCCl.O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:26]([OH:29])[C:3]=1[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 13682777HCID 13682777, compound

Product 1

HCID 178431769HCID 178431769, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled solution of 4,5-dichloro-2-methyl-pyridine-N-oxide (8.54 g) in dichloromethane (110 ml) at 10°-15°, was added trifluoroacetic anhydride (12 ml) and the reaction mixture allowed to stand 6 days. The solution was cooled to 5°-10°, methanol added dropwise and the mixture stripped. The residue was treated with H2O (70 ml) basified to pH 9-10 (K2CO3) and extracted with chloroform. The extract was dried (K2CO3), stripped and the residue triturated with petrol to give 4,5-dichloro-2-hydroxy- methylpyridine, (6.15 g), m.p. 103°-106°

Workup

  1. temperatureThe solution was cooled to 5°-10°
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried (K2CO3)
  4. customthe residue triturated with petrol

Sources & evidence

ORD record
ord-f6d2e636942741aea89c6a214b6d2a62
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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