Sodium Bicarbonate → HCID 22170382, compound

HRID 1822852Notes

Reaction equation

HRID 1822852 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.[NH2:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[CH:24][N:25]2[CH3:30].C([O-])(=O)C.[Na+].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:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[CH:24][N:25]2[CH3:30]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamideHCID 22170306476194-49-7

Product 1

HCID 22170382HCID 22170382, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarboxamide (0.028 g, 0.10 mmol), 4-amino-1-methylindol hydrochloride (0.026 g, 0.14 mmol) and sodium acetate (0.013 g, 0.16 mmol) in DMF (0.6 ml) was heated at 100° C. for 8 h. After cooling, the mixture was diluted with water and made alkaline with saturated NaHCO3. The gummy precipitate was collected and crystallized from methanol-water to give the title compound (24 mg, 60%).

Workup

  1. temperatureAfter cooling
  2. customThe gummy precipitate was collected
  3. customcrystallized from methanol-water

Sources & evidence

ORD record
ord-cc8cc54361864924abd1c78111a364b9
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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