HCID 15727118, compound → HCID 19697594, compound

HRID 863245Notes

Reaction equation

HRID 863245 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:4])=[O:3]>C(O)(=O)C.[Pt]=O>[CH3:1][S:2]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH2:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 15727118HCID 15727118, compound

Product 1

HCID 19697594HCID 19697594, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 6.5 g of 3-methylsulfonylquinoline in 200 ml of glacial acetic acid is hydrogenated in the presence of 690 mg of platinum oxide at 50° C. for 13 h. After the reaction mixture has been filtered over Celite® 545, the filtrate is concentrated and the crude product is purified by means of FC over 200 g of silica gel with a 99:1 mixture of methylene chloride and methanol as the mobile phase: Rf (K)=0.45; anal. calc. for C10H13NO2S: C56.85%, H6.20%, N6.63%; found C56.95%, H6.17%, N6.77%.

Workup

  1. filtrationAfter the reaction mixture has been filtered over Celite® 545
  2. concentrationthe filtrate is concentrated
  3. customthe crude product is purified by means of FC over 200 g of silica gel with a 99:1 mixture of methylene chloride and methanol as the mobile phase

Sources & evidence

ORD record
ord-31ab5d9a971f446f93cac22471901506
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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