HCID 59507520, compound → HCID 59507805, compound

HRID 1043781Notes

Reaction equation

HRID 1043781 reaction equation
[CH3:1][S:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([N+:15]([O-])=O)[CH:11]=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>CCOC(C)=O.[Pd]>[CH3:1][S:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([NH2:15])[CH:11]=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 59507520HCID 59507520, compound

Product 1

HCID 59507805HCID 59507805, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 7-(methylsulfonyl)-3-nitroquinoline (85 mg, 0.4 mmol) in EtOAc (6 mL) under argon, was added 10% Pd/C (22 mg, 0.04 mmol). A H2 balloon was connected to the reaction flask, the flask was purged with H2 three times and the reaction mixture was allowed to stir under H2 atmosphere for 18 h. Unreacted starting material could be seen settling to the bottom of the flask together with the catalyst. The solids were removed from the EtOAc solution by filtration. Evaporation of EtOAc under reduced pressure yielded 7-(methylsulfonyl)-3-quinolylamine (22 mg, 30%). LC/MS (m/z): 223.0 (MH+), Rt 1.10 minutes.

Workup

  1. customthe flask was purged with H2 three times
  2. customThe solids were removed from the EtOAc solution by filtration
  3. customEvaporation of EtOAc under reduced pressure

Sources & evidence

ORD record
ord-d22e4689ea76429cb798321bfc6a1358
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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