Potassium Hydroxide → HCID 20244806, compound

HRID 2418744Notes

Reaction equation

HRID 2418744 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH3:13][O:14][C:15]1[C:16](=[O:27])[NH:17][C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20](=[O:22])[CH:21]=1.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.C(OCC)(=O)C>[CH2:6]([O:5][C:3]([CH2:2][N:17]1[C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20](=[O:22])[CH:21]=[C:15]([O:14][CH3:13])[C:16]1=[O:27])=[O:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 62576Benzyl bromoacetateHCID 107506631H-1-Benzazepine-2,5-dione, 3-methoxy-

Product 1

HCID 20244806HCID 20244806, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl bromoacetate (9.16 g, 0.04 mole) was added dropwise to a mixture of 3-methoxy-2,5-dihydro-1H-[1]benzazepine-2,5-dione [8.13 g, 0.04 mole, prepared as described in the Canadian J. Chem., 52, 610 (1974)] powdered potassium hydroxide (2.24 g, 0.04 mole) and tetrabutylammonium bromide (1.29 g, 0.004 mol) in 1 L of acetonitrile with stirring at room temperature. Upon complete addition, the suspension was stirred at room temperature for 64 hours, filtered, and the filtrate concentrated under reduced pressure to give a partially crystalline oil. This oil was triturated with ether to give a solid which was suspended and stirred in ethyl acetate (100 ml) for 1.5 hours. The insoluble material was filtered off and the filtrate concentrated to give the crude 1-benzyloxycarbonylmethyl-3-methoxy-2,5-dihydro-1H-[1]benzazepin-2,5-dione which was used directly in the next step.

Workup

  1. customprepared
  2. additionUpon complete addition
  3. stirringthe suspension was stirred at room temperature for 64 hours
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto give a partially crystalline oil
  7. customThis oil was triturated with ether
  8. customto give a solid which
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-7276971596d4405db9e4154191ba7a24
Source dataset
uspto-grants-1984_09
Patent number
US04473575

Reaction notes

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