HCID 86592011, compound → HCID 86592010, compound

HRID 1785876Notes

Reaction equation

HRID 1785876 reaction equation
[CH3:1][C@H:2]1[CH2:11][C@@H:10]([N:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13](=[O:16])[CH2:14][CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:23](=[O:33])[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=1>C(O)C.[Pd]>[NH2:30][C:27]1[CH:26]=[CH:25][C:24]([C:23]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C@H:10]([N:12]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:13](=[O:16])[CH2:14][CH3:15])[CH2:11][C@@H:2]2[CH3:1])=[O:33])=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 86592011HCID 86592011, compound

Product 1

HCID 86592010HCID 86592010, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(±)-Cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide was prepared from (±)-cis-N-[2-methylmethyl-1-(4-nitro-benzoyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. (±)-Cis-N-[2-methyl-1-(4-nitro-benzoyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide (200 mg, 0.45 mmol) was dissolved in ethanol (20 mL). Palladium on carbon (10%) was carefully added and the resulting suspension was shaken under hydrogen gas (40 psi) over night. The suspension was filtered through Celite® to remove solids, and the filter cake washed three times with ethanol. Concentration of the solution afforded pure product (160 mg, 86%).

Workup

  1. filtrationThe suspension was filtered through Celite®
  2. customto remove solids
  3. washthe filter cake washed three times with ethanol

Sources & evidence

ORD record
ord-74cf2a8ed51c46379e5143067e800f17
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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