Sodium borohydride → HCID 22405055, compound

HRID 441235Notes

Reaction equation

HRID 441235 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](=[O:28])[C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH2:10][CH2:9][CH2:8]1)=[O:5])[CH3:2].[BH4-].[Na+]>CO.O1CCCC1.C(Cl)(Cl)Cl.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]([N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:8][CH2:9][CH2:10]2)=[O:28])=[CH:24][CH:23]=1

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 53827841HCID 53827841, compound

Product 1

HCID 22405055HCID 22405055, compoundYield 80.4%

Reagents, catalysts & solvents 4

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent2×HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-ethoxycarbonylmethylene-1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (671 mg) and nickel chloride hexahydrate (419 mg) in a mixture of methanol (25 ml) and tetrahydrofuran (25 ml) was added sodium borohydride (601 mg) in portions at 0° C. and the mixture was stirred at the same temperature for 30 minutes. The solution was filtered through a bed of celite and the filtrate was evaporated in vacuo. The residue was dissolved in chloroform and the solution was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo to give a crude oil and the oil was subjected to silica gel column (30 g, 1% methanol in chloroform) to give 1-(4-aminobenzoyl)-5-ethoxycarbonylmethyl-2,3,4,5-tetrahydro -1H-1-benzazepine (500 mg).

Workup

  1. filtrationThe solution was filtered through a bed of celite
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. washthe solution was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customto give a crude oil

Sources & evidence

ORD record
ord-8b44d876fa8247638b55459ab5a7c7b2
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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