Reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C:7]3[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=3[CH2:9][N:10]([C:11]([NH:13][NH2:14])=[O:12])[C:4]=2[CH:3]=1.[N:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][C:30](OC)=[O:31])=[CH:23][CH:22]=1.[Cl-].C[Al+]C.CO>C1(C)C=CC=CC=1>[O:31]=[C:30]([NH:14][NH:13][C:11]([N:10]1[CH2:9][C:8]2[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=2[O:6][C:5]2[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][C:4]1=2)=[O:12])[CH2:29][CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][N:21]=[CH:26][CH:25]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, hydrazide (1) (1.5 g, 5 mmol), prepared as described above in Example 1, and methyl 4-(4-pyridyl)butanoate (48) (2.4 g, 13 mmol), prepared as described above in Example 48, in toluene (250 mL) was added dimethylaluminumchloride (20.0 mmol). The resulting yellow solution was refluxed under a N2 atmosphere for 16 hours. The reaction mixture was allowed to cool to room temperature, followed by the addition of methanol (7 mL). The reaction mixture was extracted with sodium hydroxide (1M, 2×200 mL), and the aqueous extracts were combined and extracted with ethyl acetate (3×200 mL). The organic solutions were combined, dried (Na2SO4) and evaporated to yield 1.8 g of crude product as a thick oil.
Workup
- customprepared
- temperatureThe resulting yellow solution was refluxed under a N2 atmosphere for 16 hours
- extractionThe reaction mixture was extracted with sodium hydroxide (1M, 2×200 mL)
- extractionextracted with ethyl acetate (3×200 mL)
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-89ece8e93a4f4b2eafe3c7c96c3a21d9
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576315
Linked notes
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