5-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one → 5-(2-chloroacetyl)-8-phenylmethoxy-1H-quinolin-2-one

HRID 969454Notes

Reaction equation

HRID 969454 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:22])[NH:9]2)(=[O:3])[CH3:2].I([Cl:26])(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>ClC(Cl)C.CO>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:4]([C:1](=[O:3])[CH2:2][Cl:26])=[C:5]2[C:10]=1[NH:9][C:8](=[O:22])[CH:7]=[CH:6]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 133754445-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-oneHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 109035505-(2-chloroacetyl)-8-phenylmethoxy-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 63651,1-DichloroethaneSolvent

Procedure

25.2 g (86 mmol) 5-acetyl-8-benzyloxy-1H-quinolin-2-one (European Journal of Medicianl Chemistry 1984, 19(4), 341) and 50 g (142 mmol) benzyltrimethylammonium dichloriodate in 500 mL dichloroethane and 300 mL methanol are stirred overnight at reflux temperature. The reaction mixture is evaporated down and the residue is stirred overnight in THF and 1 N hydrochloric acid. After the THF has been distilled off the precipitated solid is suction filtered, washed with diethyl ether and dried.

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated down
  3. distillationAfter the THF has been distilled off the precipitated solid
  4. filtrationfiltered
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-a11f8d532aa14756850f9b24b7421726
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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