Methanol → HCID 19604208, compound

HRID 962913Notes

Reaction equation

HRID 962913 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:3]=1.S(=O)(=O)(O)O.[CH3:21]O>>[Cl:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([O:14][CH3:21])=[O:13])[CH:3]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 1118Sulfuric AcidHCID 19604211HCID 19604211, compound

Product 1

HCID 19604208HCID 19604208, compound

Conditions

Temperature
2 °C

Procedure

43 g of 4-(5-chloro-1,6-dihydro-6-oxopyridin-3-yl)-4-oxobutyric acid (crude product, prepared as described in Example 6) was suspended in 730 ml of methanol, and 16 ml of concentrated sulfuric acid was added. The mixture was heated in such a way that approximately 100 ml of methanol distilled off in the course of 4 hours. The reaction mixture which remained was then concentrated to half its volume under reduced pressure and the resulting solution was cooled to 2° C. The product was removed by filtration, washed using 20 ml of cold methanol and dried. The product yield was 38.1 g (83%) of white crystals. The product melting point was 211.5° to 213.5° C. Other data concerning the product was:

Workup

  1. distillationdistilled off in the course of 4 hours
  2. concentrationThe reaction mixture which remained was then concentrated to half its volume under reduced pressure
  3. customThe product was removed by filtration
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-0bd5146a5544428b9a2f6f8ed715f616
Source dataset
uspto-grants-1998_06
Patent number
US05760236

Reaction notes

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