1,2-Dichloroethane → 7-(Benzyloxy)-5-(chloroacetyl)quinolin-2(1H)-one

HRID 1372907Notes

Reaction equation

HRID 1372907 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:22])[NH:9]2)(=[O:3])[CH3:2].[Cl:23]CCCl>C(O)(=O)C.O.C(=O)(O)[O-].[Na+].S(=O)(O)[O-].[Na+]>[CH2:15]([O:14][C:12]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:22])[NH:9]2)=[C:4]([C:1](=[O:3])[CH2:2][Cl:23])[CH:13]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 2

HCID 111,2-DichloroethaneHCID 210728495-Acetyl-7-(benzyloxy)quinolin-2(1H)-one

Product 1

HCID 210728597-(Benzyloxy)-5-(chloroacetyl)quinolin-2(1H)-one

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolventHCID 23665763Sodium BisulfiteSolvent

Conditions

Temperature
65 °C

Procedure

5-acetyl-7-benzyloxy-1H-quinolin-2-one (7.0 g, 23.86 mmol) is dissolved in a mixture of 1,2-dichloroethane (147 mL), glacial acetic acid (43 mL) and water (7 mL) and combined with N-benzyl-trimethylammonium-dichloriodate (19.0 g, 54.58 mmol). The mixture is stirred for 4.5 hours at 65° C., then diluted with sodium bicarbonate solution and 5% sodium bisulphite solution and stirred for 5 minutes. The precipitate formed is filtered off, washed with water (2×20 mL) and dried in the oven. Yield: 6.0 g (77%); mass spectroscopy: [M+H]+=328.

Workup

  1. stirringstirred for 5 minutes
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water (2×20 mL)
  5. customdried in the oven

Sources & evidence

ORD record
ord-916830508d6a40c29142620275afa283
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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