Sodium Hydroxide → HCID 15168475, compound

HRID 484426Notes

Reaction equation

HRID 484426 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([C:17]([O:19]C)=[O:18])=[CH:5][C:6]([C:13]([O:15]C)=[O:14])=[N:7]2.[OH-].[Na+]>CO>[C:13]([C:6]1[CH:5]=[C:4]([C:17]([OH:19])=[O:18])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[N:7]=1)([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15168454HCID 15168454, compound

Product 1

HCID 15168475HCID 15168475, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5,7-Dichloro-2,4-dimethoxycarbonylquinoline (Example 15a) (28 g) was dissolved in 50% aqueous methanol (700ml) with sodium hydroxide (35.8 g) and the solution was heated at reflux for 18 h. After cooling, the methanol was removed by evaporation and the residue was diluted with water to a volume of approximately 700 ml. Concentrated hydrochloric acid was added to the aqueous solution at 90° C. and the white solid produced was filtered while the filtrate was still hot. The solid was dried in a vacuum oven at 100° C. (20 mmHg) for 48 h to give the title compound (19.5 g, m.p. 246° C.);δ (360 MHz, DMSO) 8.09 (1H, s, 3-H), 8.13 (1H, d, J=2.2 Hz, 6-H or 8-H), 8.32 (1H, d, J=2.2 Hz, 6-H or 8H); m/e 354 (M+); Found: C, 43.48 ; H, 2.45; N, 4.58% C11H5Cl2NO4.H2O requires C, 43.45; H, 2.32; N, 4.61%

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 18 h
  3. temperatureAfter cooling
  4. customthe methanol was removed by evaporation
  5. additionthe residue was diluted with water to a volume of approximately 700 ml
  6. additionConcentrated hydrochloric acid was added to the aqueous solution at 90° C.
  7. customthe white solid produced
  8. filtrationwas filtered while the filtrate
  9. customThe solid was dried in a vacuum oven at 100° C. (20 mmHg) for 48 h

Sources & evidence

ORD record
ord-465cf035e68a44669251e915d0e13cfa
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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