Acetic Acid → HCID 22170189, compound

HRID 1822845Notes

Reaction equation

HRID 1822845 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].[C:19](O)(=O)[CH3:20].[OH-].[Na+].C[N:26]([CH:28]=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:26][C:28]1[C:20]2[CH2:19][CH2:8][CH2:9][CH2:10][C:11]=2[CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Product 1

HCID 22170189HCID 22170189, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarboxamide (0.090 g, 0.34 mmol), 5,6,7,8-tetrahydronaftylamine (0.062 g, 0.42 mmol) and acetic acid (80 μl) in DMF (1.6 ml) was heated at 100° C. for 3.5 h. After cooling the reaction mixture was diluted with water (20 ml) and made alkaline with 1 M NaOH. The precipitate was filtered, rinsed with water and dried to give the title compound (62 mg, 48%).

Workup

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

Sources & evidence

ORD record
ord-dfda4ecd3f204e0d94853f3bc9d4a257
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

Loading…