Sodium Hydroxide → 3-H-epoxybenzazepin
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]=12Participants
3
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
- custompartitioned between H2O and CH2Cl2
- dry with materialthe organic layer dried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-240ac636d3dc406da72190283b4e800a
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04855426
Reaction notes
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