Acetic Acid → HCID 22170208, compound

HRID 1822855Notes

Reaction equation

HRID 1822855 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([NH2:18])=[O:17].[NH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[C:22](C)[CH:21]=1.[C:30](O)(=O)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[C:24]([C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]([NH2:18])=[O:17])=[C:28]([CH3:30])[CH:27]=1)([OH:26])=[O:25]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 2416324-amino-2-methylbenzoic acidHCID 516892Sodium BicarbonateHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Product 1

HCID 22170208HCID 22170208, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarboxamide (0.046 g, 0.17 mmol), 4-amino-2-methylbenzoic acid (0.036 g, 0.24 mmol) and acetic acid (40 μl) in DMF (0.8 ml) was heated at 100° C. for 12 h. After cooling, the mixture was diluted with water (15 ml) and made alkaline with saturated NaHCO3 and was then weakly acidified with acetic acid. The precipitate was filtered of and suspended in warm methanol. After cooling, the precipitate was filtered off and dried to give the title compound (31 mg, 47%).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered of and
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-f0c8b768ece74532b5d2bff9a928e2a5
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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