2-[N-methyl-N-(4-nitrophenyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one → HCID 23287735, compound

HRID 367188Notes

Reaction equation

HRID 367188 reaction equation
[CH3:1][N:2]([C:12]1[S:13][C:14]2[N:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16](=[O:18])[N:17]=1)[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][CH:4]=1.[H][H]>[Ni].CN(C=O)C>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([C:12]2[S:13][C:14]3[N:22]=[CH:21][CH:20]=[CH:19][C:15]=3[C:16](=[O:18])[N:17]=2)[CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 232877462-[N-methyl-N-(4-nitrophenyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 23287735HCID 23287735, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.505 g (4.79 mmol) of 2-[N-methyl-N-(4-nitrophenyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one obtained in Example 63, 50 ml of DMF and about 1.5 g of Raney nickel was stirred in an atmosphere of hydrogen for 5 hours. The resulting insoluble matters were then removed by filtration. The resulting filtrate was then concentrated under reduced pressure. The residue was then recrystallized from ethanol to obtain 984 mg of 2-[N-(4-aminophenyl)-N-methylamino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. customThe resulting insoluble matters were then removed by filtration
  2. concentrationThe resulting filtrate was then concentrated under reduced pressure
  3. customThe residue was then recrystallized from ethanol

Sources & evidence

ORD record
ord-83e71e5cfb404f59ac72f313591cd657
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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