HCID 19607917, compound → HCID 10692311, compound

HRID 745076Notes

Reaction equation

HRID 745076 reaction equation
[N:1]([CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15](=[O:32])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:30])=[CH:18][CH:17]=2)[CH2:7][CH2:6][CH2:5]1)=[N+]=[N-].[H][H]>C(O)C.[Pd]>[NH2:1][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15](=[O:32])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:30])=[CH:18][CH:17]=2)[CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 19607917HCID 19607917, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10692311HCID 10692311, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Azido-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.63 g) is dissolved in ethanol and thereto is added 10% Pd-C (0.1 g). The mixture is subjected to catalytic hydrogenation at room temperature under 1 atm. of hydrogen. Pd-C is removed by filtration and the filtrate is evaporated. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1), and recrystallized from diethyl ether to give 5-amino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.34 g) as white powder, m.p. 198.5°-199.5° C.

Workup

  1. customPd-C is removed by filtration
  2. customthe filtrate is evaporated
  3. customThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1)
  4. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-c370886228364389b7fbd063a929bffb
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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