Acetic Acid → HCID 22170208, compound

HRID 1822846Notes

Reaction equation

HRID 1822846 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]([CH3:29])=[C:22](C=[CH:27][CH:28]=1)C(O)=O.[C:30]([OH:33])(=[O:32])[CH3:31]>CS(C)=O>[C:30]([C:31]1[CH:27]=[CH:28][C:20]([NH:19][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]([NH2:18])=[O:17])=[C:21]([CH3:29])[CH:22]=1)([OH:33])=[O:32]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 27336993-Amino-2-methylbenzoic acidHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Product 1

HCID 22170208HCID 22170208, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarboxamide (0.046 g, 0.17 mmol), 3-amino-2-methylbenzoic acid (0.035 g, 0.23 mmol) and acetic acid (40 μl) in DMSO (0.8 ml) was stirred at 100° C. for 5 h. After cooling the reaction mixture was washed several times with diethyl ether. The oily residue was dissolved in water and made alkaline with 1 M NaOH and then weakly acidified with acetic acid. The mixture was left at 5° C. over night and the resulting precipitate was collected by filtration, washed with water and dried to give the title compound (35 mg, 50%).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washwas washed several times with diethyl ether
  3. dissolutionThe oily residue was dissolved in water
  4. waitThe mixture was left at 5° C. over night
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-7d6e4e32970247798aca14ee681c7bbb
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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