2(1h)-Quinolinone,3-(2,6-dichloro-3-nitrophenyl)-1-methyl- → HCID 59833914, compound

HRID 270701Notes

Reaction equation

HRID 270701 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[C:13](=[O:23])[N:14]([CH3:22])[C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2>CCO.Cl.CCOC(C)=O.C([O-])([O-])=O.[K+].[K+]>[NH2:8][C:7]1[C:2]([Cl:1])=[C:3]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]([Cl:11])=[CH:5][CH:6]=1

Participants

6

Reactant 1

HCID 598338082(1h)-Quinolinone,3-(2,6-dichloro-3-nitrophenyl)-1-methyl-

Product 1

HCID 59833914HCID 59833914, compoundYield 96.8%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
75 °C

Procedure

To a suspended solution of 3-(2,6-dichloro-3-nitro-phenyl)-1-methyl-1H-quinolin-2-one (50 mg, 0.143 mmol) in EtOH (3.0 mL) is added a solution of Sn(II)Cl2 (122 mg, 0.644 mmol) in concentrated HCl (2.0 mL) at 75° C. After the mixture is stirred for 30 minutes at 75° C., the mixture is diluted with EtOAc and neutralized with K2CO3 until a pH of 8 is achieved. The organic layer is washed with saturated K2CO3, brine and dried, filtered and concentrated to give crude product (44.2 mg, 96.7%).

Workup

  1. washThe organic layer is washed with saturated K2CO3, brine
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-04caf6308d99451b8a3890fe4dd305a4
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Reaction notes

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