Methanol → 5-ethoxycarbonylmethyl-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1291550Notes

Reaction equation

HRID 1291550 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC([CH:11]1[C:17]2[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=2[N:15]([C:23](=[O:41])[C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:39])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])=[CH:26][C:25]=2[CH3:40])[C:14](=C)[CH2:13][CH2:12]1)=O)C.[BH4-].[Na+].C[OH:46]>O.O.O.O.O.O.[Ni](Cl)Cl>[CH2:2]([O:1][C:5]([CH2:4][CH:11]1[C:17]2[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=2[N:15]([C:23](=[O:41])[C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:39])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])=[CH:26][C:25]=2[CH3:40])[CH2:14][CH2:13][CH2:12]1)=[O:46])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 867525795-ethoxycarbonyl-methylidene-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

Product 1

HCID 189173165-ethoxycarbonylmethyl-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

In 30 ml of a 1:1 mixture of tetrahydrofuran and methanol were dissolved 0.30 g of 5-ethoxycarbonyl-methylidene-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine and 0.55 g of nickel chloride hexahydrate. Thereto was slowly added 0.26 g of sodium borohydride with ice-cooling and stirring. The mixture was stirred for 10 minutes with ice-cooling. The resulting insolubles were removed by filtration with Celite. The filtrate was concentrated. The residue was purified by silica gel column chromatography (elutant: ethyl acetate/n-hexane =1/1) to obtain 0.13 g of 5-ethoxycarbonylmethyl-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 10 minutes with ice-
  3. temperaturecooling
  4. customThe resulting insolubles were removed by filtration with Celite
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography (elutant: ethyl acetate/n-hexane =1/1)

Sources & evidence

ORD record
ord-358e969db782416e8ae205cfadca79cc
Source dataset
uspto-grants-1998_05
Patent number
US05753644

Reaction notes

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