Water → HCID 22405272, compound

HRID 441234Notes

Reaction equation

HRID 441234 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[N+:17]([C:20]1[CH:38]=[CH:37][C:23]([C:24]([N:26]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:25])=[CH:22][CH:21]=1)([O-:19])=[O:18].O>O1CCCC1>[CH2:13]([O:12][C:10]([CH:9]=[C:30]1[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N:26]([C:24](=[O:25])[C:23]2[CH:37]=[CH:38][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)[CH2:27][CH2:28][CH2:29]1)=[O:11])[CH3:14].[CH2:13]([O:12][C:10]([CH2:9][C:30]1[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N:26]([C:24](=[O:25])[C:23]2[CH:37]=[CH:38][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)[CH2:27][CH2:28][CH:29]=1)=[O:11])[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 106376761H-1-Benzazepine, 2,3,4,5-tetrahydro-1-(4-nitrobenzoyl)-

Product 2

HCID 22405272HCID 22405272, compoundHCID 53827841HCID 53827841, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl diethylphosphonoacetate (6.10 g) in tetrahydrofuran (50 ml) was added sodium hydride (60% in oil, 599 mg) and the solution was stirred at ambient temperature for 30 minutes. To the solution was added a solution of 1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro -1H-1-benzazepine (3.10 g) in tetrahydrofuran (10 ml) dropwise and the mixture was stirred at ambient temperature for 5 hours. The solution was poured into water and the aqueous solution was extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the crude product was purified by silica gel column (100 g, 1% methanol in chloroform) to give 5-ethoxycarbonylmethylene-1-(4-nitrobenzoyl) -2,3,4,5-tetrahydro-1H-1-benzazepine (689 mg) and 5-ethoxycarbonylmethyl-1-(4-nitrobenzoyl)-2,3-dihydro -1H-1-benzazepine (905 mg).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 5 hours
  2. extractionthe aqueous solution was extracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe crude product was purified by silica gel column (100 g, 1% methanol in chloroform)

Sources & evidence

ORD record
ord-8c569f559cc44cd0ae4bf21d958e745c
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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