Hydrochloric Acid → HCID 19077582, compound

HRID 964600Notes

Reaction equation

HRID 964600 reaction equation
[CH3:1][O-:2].[Na+].CO.Cl[C:7]1[N:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2/[C:21](=[N:26]\[O:27][CH3:28])/[C:22]([NH:24][CH3:25])=[O:23])[CH:10]=[CH:9][CH:8]=1.Cl>O>[CH3:1][O:2][C:7]1[N:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2/[C:21](=[N:26]\[O:27][CH3:28])/[C:22]([NH:24][CH3:25])=[O:23])[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 19077581HCID 19077581, compound

Product 1

HCID 19077582HCID 19077582, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

28% sodium methoxide--methanol solution (1.16 g) was added to (E)-2-[2-(6-chloropyridin-2-yloxymethyl)phenyl]-2-methoxyimino-N-methylacetamide (400 mg), and the mixture was heated under reflux with stirring for 4 hours. The mixture was neutralized with 1N hydrochloric acid, and water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried, and the solvent was evaporated. The resulting oil was purified by column chromatography on silica gel to give the title compound (61 mg). mp. 81°-82° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. customthe solvent was evaporated
  8. customThe resulting oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-908f55e533e04cc39eeab4c1136beaa5
Source dataset
uspto-grants-1998_06
Patent number
US05770614

Reaction notes

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