Acetic Acid → HCID 22170188, compound

HRID 1822848Notes

Reaction equation

HRID 1822848 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].[Cl:19][C:20]1[C:21]([CH3:27])=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].C(O)(=O)C.[OH-].[Na+]>CN(C=O)C.O>[Cl:19][C:20]1[C:21]([CH3:27])=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH:23][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]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 68943-Chloro-2-methylanilineHCID 14798Sodium HydroxideHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Product 1

HCID 22170188HCID 22170188, compoundYield 80.7%

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), 3-chloro-2-methylaniline (25 μl, 0.21 mmol) and acetic acid (40 μl) in DMF (0.8 ml) was heated at 100° C. for 4.5 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 (51 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-2d5669267da14c1cbf242f736299555c
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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