Water → 3-Butyryl-4-(2-chlorophenylamino)8-(2-methylsulfinylethoxy)quinoline

HRID 1419873Notes

Reaction equation

HRID 1419873 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:24][CH2:25][CH2:26][S:27][CH3:28])(=[O:5])[CH2:2][CH2:3][CH3:4].[OH2:29].Cl[O-].[Na+]>C(Cl)Cl>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:24][CH2:25][CH2:26][S:27]([CH3:28])=[O:29])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 23665760Sodium Hypochlorite2×HCID 544124113-Butyryl-4-(2-chlorophenylamino)-8-(2-methylthioethoxy)quinoline

Product 1

HCID 539526483-Butyryl-4-(2-chlorophenylamino)8-(2-methylsulfinylethoxy)quinolineYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-butyryl-4-(2-chlorophenylamino)-8-(2-methylthioethoxy)quinoline (0.34g, 0.82 mmol) was dissolved in methylene chloride (4 ml). Water (2 ml) and sodium hypochlorite (5% in water) (1.37 ml) were added and the mixture was stirred for 2 h. Another portion of sodium hypochlorite (0.5 ml) was added and the stirring was continued for 2 h. The organic layer was dried over sodium sulfate and evaporated. The residue crystallized from a mixture of ethyl acetate and isopropyl ether and 0.25 g (71%) of the title compound was obtained.

Workup

  1. waitthe stirring was continued for 2 h
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated
  4. customThe residue crystallized from a mixture of ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-030166e33cd94709a79a886d54790fea
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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