3-(2,6-dichloro-3-nitro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one → 3-(3-amino-2,6-dichloro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one

HRID 270696Notes

Reaction equation

HRID 270696 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][N: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][N:18]=[CH:17][CH:16]=3)[C:4]([Cl:11])=[CH:5][CH:6]=1

Participants

6

Reactant 1

HCID 598338673-(2,6-dichloro-3-nitro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one

Product 1

HCID 598338933-(3-amino-2,6-dichloro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-oneYield 93.15%

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-[1,6]naphthyridin-2-one (1.55 g, 4.427 mmol) in EtOH (12 mL) is added a solution of Sn(II)Cl2 (3.80 g, 19.92 mmol) in HCl (con. 16 mL) at 75° C. After stirring for 30 minutes at 75° C., the mixture is diluted with EtOAc and neutralized with K2CO3 to a pH of 8. The organic layer is washed with saturated K2CO3, brine and dried, filtered and concentrated to give crude product. The crude product is purified by recrystallization with CH2Cl2/EtOAc/Hexane to give the titled intermediate as a solid (1.32 g, 93.15%).

Workup

  1. washThe organic layer is washed with saturated K2CO3, brine
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product
  6. customThe crude product is purified by recrystallization with CH2Cl2/EtOAc/Hexane

Sources & evidence

ORD record
ord-9e282313f2c9408c90b39426336e0c8f
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Reaction notes

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