Methanol → HCID 15168480, compound

HRID 484427Notes

Reaction equation

HRID 484427 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[C:11]2[C:6](=[CH:7][C:8]([Cl:18])=[CH:9][C:10]=2[Cl:17])[N:5]=1)([OH:3])=[O:2].[CH3:19]O>>[C:14]([C:12]1[C:11]2[C:6](=[CH:7][C:8]([Cl:18])=[CH:9][C:10]=2[Cl:17])[N:5]=[C:4]([C:1]([O:3][CH3:19])=[O:2])[CH:13]=1)([OH:16])=[O:15]

Participants

3

Reactant 2

HCID 887MethanolHCID 15168475HCID 15168475, compound

Product 1

HCID 15168480HCID 15168480, compound

Procedure

2,4-Dicarboxy-5,7-dichloroquinoline was added to methanol (presaturated with dry hydrogen chloride) (500 ml) and the solution left at room temperature for 1 h. After this time the volume of solvent was reduced to approximately 100 ml and the white solid that precipitated was collected by filtration and dried in a vacuum oven at 100° C. (20 mm Hg) for 2 h to give the title compound (18.5 g, m.p. 260°-262° C.); δ (250 MHz, DMSO) 3.98 (3H, s, CH3), 8.11 (1H, s, 3-H), 8.15 (1H, d, J=2.1 Hz, 6-H or 8-H), 8.36 (1H, d, J=2.1 Hz, 6-H or 8-H); m/e 299 (M+) 241 (100%, M-CO2CH3 +H); Found: C, 47.58; H, 2.42; N, 4.62. C12H7Cl2NO4. 0.2 H2O requires C, 47.46; H, 2.46; N, 4.61%.

Workup

  1. customthe white solid that precipitated
  2. filtrationwas collected by filtration
  3. customdried in a vacuum oven at 100° C. (20 mm Hg) for 2 h

Sources & evidence

ORD record
ord-74068b487f9d4033a779343dcadf7a99
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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