Methanol → HCID 14154315, compound

HRID 231155Notes

Reaction equation

HRID 231155 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[N+:4]([O-])[C:3]=1[CH3:11].C(OC(=O)C)(=[O:14])C.CO>C(O)(=O)C>[Cl:1][C:2]1[C:3]([CH2:11][OH:14])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 13682775HCID 13682775, compound

Product 1

HCID 14154315HCID 14154315, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

5.8 g of 3-chloro-4-methoxy-2-picoline-N-oxide were dissolved in 8 ml of glacial acetic acid and, while stirring at 90° C., 14 ml of acetic anhydride were added. The mixture was heated at 110°-115° C. for 2 hours and then cooled to 80° C. and 25 ml of methanol were added dropwise. The solvent was then removed by distillation under reduced pressure, and subsequently 20 ml of water and 8 g of sodium hydroxide were added in small portions to the residue, and this mixture was heated to reflux for 2 hours. After cooling, the mixture was extracted with dichloromethane, the solvent was evaporated off, and the residue is induced to crystallize with diethyl ether. Solid, melting point 103°-105° C.

Workup

  1. temperatureThe mixture was heated at 110°-115° C. for 2 hours
  2. temperaturecooled to 80° C.
  3. customThe solvent was then removed by distillation under reduced pressure, and subsequently 20 ml of water and 8 g of sodium hydroxide
  4. additionwere added in small portions to the residue
  5. temperaturethis mixture was heated
  6. temperatureto reflux for 2 hours
  7. temperatureAfter cooling
  8. extractionthe mixture was extracted with dichloromethane
  9. customthe solvent was evaporated off
  10. customto crystallize with diethyl ether

Sources & evidence

ORD record
ord-d172e5433ce946589a2c92fc98a3f71d
Source dataset
uspto-grants-1989_07
Patent number
US04845118

Reaction notes

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