Acetic Acid → 4-(3-Hydroxy-2-methylanilino)-6,7-dimethoxy-3-quinolinecarboxamide

HRID 1822850Notes

Reaction equation

HRID 1822850 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[C:21]([CH3:27])=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.C(O)(=O)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[OH:26][C:22]1[C:21]([CH3:27])=[C:20]([CH:25]=[CH:24][CH:23]=1)[NH:19][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 1044482-Amino-o-cresolHCID 516892Sodium BicarbonateHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Product 1

HCID 221702874-(3-Hydroxy-2-methylanilino)-6,7-dimethoxy-3-quinolinecarboxamide

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-amino-2-methylphenol (0.032 g, 0.26 mmol) and acetic acid (40 μl) in DMF (0.8 ml) was heated at 100° C. for 1.5 h. After cooling, the mixture was diluted with water (15 ml) and made alkaline with saturated NaHCO3. The title compound, which slowly precipitated was filtered off and dried to give 34 mg (55%).

Workup

  1. temperatureAfter cooling
  2. customThe title compound, which slowly precipitated
  3. filtrationwas filtered off
  4. customdried
  5. customto give 34 mg (55%)

Sources & evidence

ORD record
ord-6ac3fe1c14f142949459a367b77b9200
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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