Acetic Acid → HCID 22170285, compound

HRID 1822844Notes

Reaction equation

HRID 1822844 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].[CH3:19][C:20]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22].C(O)(=O)C.[OH-].[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:22][C:21]1[CH:23]=[CH:24][CH:25]=[C:26]([CH3:27])[C:20]=1[CH3:19]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 68932,3-DimethylanilineHCID 14798Sodium HydroxideHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Product 1

HCID 22170285HCID 22170285, compoundYield 80.4%

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), 2,3-dimethylaniline (20 μl, 0.22 mmol) and acetic acid (40 μl) in DMF (0.8 ml) was heated at 100° C. for 3.5 h. After cooling the reaction mixture was diluted with water (15 ml) and made alkaline with 1 M NaOH. The precipitate was collected by filtration, rinsed with water and dried to give the title compound (48 mg, 79%).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationThe precipitate was collected by filtration
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-93a6a7ff812e4ba888a1eeeb4735c3c4
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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