Thiotepa → 4-amino-7-chloro-3-(3,5-dimethylphenyl)-6-nitro-1H-quinolin-2-one

HRID 1857644Notes

Reaction equation

HRID 1857644 reaction equation
[Cl:1][C:2]1[C:3]([N+:22]([O-:24])=[O:23])=[CH:4][C:5]([C:20]#[N:21])=[C:6]([NH:8][C:9](=[O:19])[CH2:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=2)[CH:7]=1.C1N(P(N2CC2)(N2CC2)=S)C1.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[NH2:21][C:20]1[C:5]2[C:6](=[CH:7][C:2]([Cl:1])=[C:3]([N+:22]([O-:24])=[O:23])[CH:4]=2)[NH:8][C:9](=[O:19])[C:10]=1[C:11]1[CH:12]=[C:13]([CH3:18])[CH:14]=[C:15]([CH3:17])[CH:16]=1

Participants

6

Reactant 3

HCID 5453ThiotepaHCID 24758Sodium hydrideHCID 22129995N-(5-chloro-2-cyano-4-nitrophenyl)-2-(3,5-dimethylphenyl)acetamide

Product 1

HCID 221299864-amino-7-chloro-3-(3,5-dimethylphenyl)-6-nitro-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(5-chloro-2-cyano-4-nitrophenyl)-2-(3,5-dimethylphenyl)acetamide (prepared essentially as described in EXAMPLE 10, StepA, 250 mg in 7 mL N,N-dimethylformamide) was added 46 mg of 95% sodium hydride and the mixture stirred at room temperature. After 1.5 hours, the reaction mixture was diluted with ethyl acetate and quenched by the careful addition of 10% aqueous sodium bisulfate. The organics were then washed with brine and dried over sodium sulfate and concentrated in vacuo. The residue was suspended in methylene chloride and the solids collected by filtration and dried in vacuo to give the title compound (188 mg).

Workup

  1. customquenched by the careful addition of 10% aqueous sodium bisulfate
  2. washThe organics were then washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationthe solids collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ee61194890d443f98c11e6994f666a65
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

Loading…