Acetic Acid → HCID 22170192, compound

HRID 1822841Notes

Reaction equation

HRID 1822841 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]([CH3:28])=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][OH:24].C(O)(=O)C.N>CCO>[OH:24][CH2:23][C:22]1[C:21]([CH3:28])=[C:20]([CH:27]=[CH:26][CH:25]=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

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 577175(3-Amino-2-methylphenyl)methanolHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Product 1

HCID 22170192HCID 22170192, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarboxamide (0.15 g, 0.56 mmol), 3-amino-2-methylbenzylalcohol (0.1 g, 0.73 mmol), acetic acid (0.2 ml) in EtOH (10 ml) was refluxed for 4 h. After cooling the pH was adjusted to 9 with aqueous NH3. The resulting precipitate was filtered off and washed with cold EtOH and dried in vaccum at 40° C. to give 0.1 g (49% yield) of the title compound.

Workup

  1. temperaturewas refluxed for 4 h
  2. temperatureAfter cooling the pH
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with cold EtOH
  5. customdried in vaccum at 40° C.

Sources & evidence

ORD record
ord-d3040d60152c400f9a2ceff1bceb0600
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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