HCID 67441592, compound → HCID 67443125, compound

HRID 1801377Notes

Reaction equation

HRID 1801377 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=2)[N:4]=[C:3]1[C:16]1[CH:21]=[CH:20][C:19]([S:22](=[O:26])(=[O:25])[NH:23][CH3:24])=[CH:18][CH:17]=1>O1CCCC1.CO.[Pd]>[CH3:1][C:2]1([CH3:27])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:17]=[CH:18][C:19]([S:22](=[O:26])(=[O:25])[NH:23][CH3:24])=[CH:20][CH:21]=1

Participants

5

Reactant 1

HCID 67441592HCID 67441592, compound

Product 1

HCID 67443125HCID 67443125, compoundYield 60.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask, Pd/C (100 mg, 40%) was added to a solution of methyl 3,3-dimethyl-2-(4-(N-methylsulfamoyl)phenyl)-3,4-dihydroquinoline-6-carboxylate (230 mg, 0.81 mmol) in tetrahydrofuran (10 mL) and methanol (10 mL). The resultant mixture was allowed to stir at room temperature for 10 hours under H2 pressure. Filtered and concentrated to provide methyl 3,3-dimethyl-2-(4-(N-methylsulfamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate as a white solid (190 mg). MS (ES+APCI) M+1=389.1.

Workup

  1. filtrationFiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ee805dee94654396979e318697eb6075
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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