HCID 11568302, compound → HCID 11551968, compound

HRID 1441935Notes

Reaction equation

HRID 1441935 reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19](=[O:28])[NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19](=[O:28])[NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 11568302HCID 11568302, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11551968HCID 11551968, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Nitrogen flushed mixture of 4-bromo-phenyl-carbamic acid 1-benzyl-1,2,3,4-tetrahydro-quinolin-6-yl ester (0.655 g., 1.5 mmol) and 5% Pd—C (0.06 g.) in absolute ethanol (20 ml) was shaken in a par apparatus at room temperature (40° C.) under 50 psi pressure of hydrogen for 5 hours. Then Pd—C was discarded through filtration. The reaction mixture was concentrated under reduced pressure and the residue was washed with dichloromethane (2×3ml) to give 2f; yield: 0.48 g. (92.3%), m.p: 198° C., C16H15BrN2O2; 1H NMR δ ppm (DMSO): 1.82-2.00 (bs, 2H), 2.76 (t, 2H), 3.27 (t, 2H), 7.01-7.08 (m, 3H), 7.25-7.39 (m, 4H), 10.14 (s, 1H), IR vmax (KBr) (cm−1): 506, 608, 690, 749, 814, 884, 927, 1005, 1211, 1265, 1319, 1354, 1401, 1440, 1501, 1550, 1601, 1748, 1938, 2370, 2779, 2725, 2767, 2823, 2922, 3262, 3420, 3774.

Workup

  1. customNitrogen flushed
  2. filtrationThen Pd—C was discarded through filtration
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe residue was washed with dichloromethane (2×3ml)

Sources & evidence

ORD record
ord-3337ad36a14549fba632efd3bd934c0a
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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