Sodium Hydroxide → 3-H-epoxybenzazepin

HRID 1165462Notes

Reaction equation

HRID 1165462 reaction equation
C(O)(=O)C(O)=O.[O:7]1[CH:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH:8]1[CH2:9][NH:10][CH2:11]2.[OH-].[Na+]>>[N:10]1[C:9]2[CH:8]=[CH:14][CH:15]=[CH:16][C:17]=2[CH:18]=[CH:13][CH:12]2[O:7][C:11]=12

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 142087342,3,4,5-Tetrahydro-1H-1,5-epoxybenzo[d]azepine oxalate

Product 1

HCID 867423053-H-epoxybenzazepinYield 103.8%

Procedure

The product prepared in Example 19 (3.85 g, 0.15M) was made basic with NaOH, partitioned between H2O and CH2Cl2, and the organic layer dried (Na2SO4) and evaporated to give the 3-H-epoxybenzazepin (2.50 g, 0.015M). This compound was treated with propionic anhydride (10 ml) and allowed to stir for two hours. Excess propionic anhydride was removed in vacuo to give 3-propoxy-epoxybenzazepin as a white solid (3.3 g, 98% yield).

Workup

  1. custompartitioned between H2O and CH2Cl2
  2. dry with materialthe organic layer dried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-766f6168eb3642358a1e3f9099485473
Source dataset
uspto-grants-1990_03
Patent number
US04910198

Reaction notes

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