Hydrochloric Acid → HCID 54717980, compound

HRID 649189Notes

Reaction equation

HRID 649189 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[C:11](=[O:23])[N:12]([CH3:22])[C:13]3[C:18]([C:19]=2[O:20]C)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+]>>[C:1]1([NH:7][C:8]([C:10]2[C:11](=[O:23])[N:12]([CH3:22])[C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[N:12]1[CH:13]=[CH:18][CH:19]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20142669HCID 20142669, compound

Product 1

HCID 54717980HCID 54717980, compound

Procedure

A mixture of one part of N-phenyl-1,2-dihydro-4-methoxy-1-methyl-2-oxo-quinoline-3-carboxamide (prepared according to Example 6) and 5 parts of 5 molar aqueous hydrochloric acid is refluxed for 2.5 h, cooled to room temperature and then neutralized with aqueous sodium hydroxide solution. The crystalline product obtained is filtered off and recrystallized from pyridine to give N-phenyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide (1) (the same compound as 1:1). M.p. 199°-200° C.

Workup

  1. temperatureis refluxed for 2.5 h
  2. customThe crystalline product obtained
  3. filtrationis filtered off
  4. customrecrystallized from pyridine

Sources & evidence

ORD record
ord-9661cd0a5b6d40baa05284dc4ffcbf5a
Source dataset
uspto-grants-1988_04
Patent number
US04738971

Reaction notes

Loading…