HCID 54269052, compound → HCID 19607757, compound

HRID 1291658Notes

Reaction equation

HRID 1291658 reaction equation
C(O[N:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])=[CH:20][CH:19]=2)[CH2:9][CH2:8][CH2:7]1)(=O)C>C(O)(=O)C.[Pt]=O>[NH2:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])=[CH:20][CH:19]=2)[CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 1

HCID 54269052HCID 54269052, compound

Product 1

HCID 19607757HCID 19607757, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-acetyloxyimino-1-[4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.48 g) in acetic acid (20 ml) is added platinum oxide (0.05 g) and the mixture is subjected to catalytic reduction under hydrogen atmosphere. After completion of the reaction, the catalyst is removed by filtration, and the filtrate is concentrated. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1→10:1), and recrystallized from ethanol/diethyl ether to give 5-amino-1-[4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.19 g) as colorless prisms, m.p. 176°-178° C.

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. customThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1→10:1)
  5. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-2b99bf9ab093485c9654ae990ff0a12b
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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