Acetic Acid → HCID 22170299, compound

HRID 1822856Notes

Reaction equation

HRID 1822856 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:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22](C)[CH:21]=1.[C:31](O)(=O)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][C:3]([C:16]([NH2:18])=[O:17])=[C:2]2[NH:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:28][C:29]=1[CH3:31]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 11672721Methyl 4-amino-2-methylbenzoateHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide2×

Product 1

HCID 22170299HCID 22170299, 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, 0.35 mmol), methyl 4-amino-2-methylbenzoate acid (0.076 g, 0.46 mmol) and acetic acid (100 μl) in DMF (0.8 ml) was heated at 100° C. for 9 h. After cooling, the mixture was combined with two similar reaction mixtures (starting from 92 and 46 mg 4-chloro-6,7-dimethoxy-3-quinolinecarboxamide respectively) and diluted with water. The mixture was made alkaline with saturated NaHCO3 and the gummy precipitate was collected, washed with water and re-crystallized from methanol to give the title compound (130 mg, 47%).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was combined with two similar reaction mixtures (
  3. customthe gummy precipitate was collected
  4. washwashed with water
  5. customre-crystallized from methanol

Sources & evidence

ORD record
ord-5d31ef5c4585439dab97d4e3891dc41e
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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