Methanol → HCID 19788063, compound

HRID 1656389Notes

Reaction equation

HRID 1656389 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:16][C:15](=[O:17])[C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=1)[CH2:2][CH3:3].[CH3:21]O>S(=O)(=O)(O)O.C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:16][C:15](=[O:17])[C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 887MethanolHCID 18404754HCID 18404754, compound

Product 1

HCID 19788063HCID 19788063, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6212ChloroformSolvent

Procedure

A stirred mixture of 6-(2-propoxyphenyl)-1,2-dihydro-2-oxopyridine-3-carboxylic acid, (0.9 g) dry methanol (30 ml) and 3 drops of concentrated sulphuric acid was heated under reflux for ca 24 hours. The cooled mixture was evaporated to yield a pale yellow solid which was dissolved in chloroform, extracted with dilute aqueous potassium carbonate (2×10 ml), washed with water and brine, dried (magnesium sulphate) and evaporated to yield a yellow solid, 0.8 g, m.p. 126°-7° C. This was recrystallised from aqueous methanol (20 ml) to yield the pure title compound, 0.65 g, m.p. 126.5°-127.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for ca 24 hours
  3. customThe cooled mixture was evaporated
  4. customto yield a pale yellow solid which
  5. extractionextracted with dilute aqueous potassium carbonate (2×10 ml)
  6. washwashed with water and brine
  7. dry with materialdried (magnesium sulphate)
  8. customevaporated
  9. customto yield a yellow solid, 0.8 g, m.p. 126°-7° C
  10. customThis was recrystallised from aqueous methanol (20 ml)

Sources & evidence

ORD record
ord-080b64f880854efa907e24d3cecf87c2
Source dataset
uspto-grants-1993_10
Patent number
US05254571

Reaction notes

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