Ethanol → HCID 19592684, compound

HRID 613572Notes

Reaction equation

HRID 613572 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH3:23].C([OH:26])C>C(O)(=O)C.Cl>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[C:13]([NH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[NH:5][CH:4]=[C:3]([CH3:23])[C:2]2=[O:26])=[O:22]

Participants

5

Reactant 2

HCID 702EthanolHCID 19592456HCID 19592456, compound

Product 1

HCID 19592684HCID 19592684, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-chloro-8-(2,6-dichlorobenzoylamino)-3-methylquinoline (500 mg) in acetic acid (16 ml) and 6N hydrochloric acid (20 ml) was heated at 130° C. for 5 days. The mixture was concentrated in vacuo and the precipitate was collected and washed with water. The residue was purified by a silica gel column chromatography (methanol:methylene chloride=1:20, V/V) to give a yellow crystal. The solid was treated with hot ethanol (5 ml), allowed to cool to ambient temperature, filtered and washed with water to give 8-(2,6-dichlorobenzoylamino)-1,4-dihydro-3-methyl-4-oxoquinoline (280 mg) as yellow crystal.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe precipitate was collected
  3. washwashed with water
  4. customThe residue was purified by a silica gel column chromatography (methanol:methylene chloride=1:20, V/V)
  5. customto give a yellow crystal
  6. filtrationfiltered
  7. washwashed with water

Sources & evidence

ORD record
ord-3c488f09bb67423fa45bd4f52e7698db
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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