Ethanol, reaction products with ammonia, distn. residues → HCID 11127710, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8](=[CH:13][C:14]#[N:15])[C:7]=2[CH:16]=1.N.C(O)C>C(O)C.[Ni]>[NH2:15][CH2:14]/[CH:13]=[C:8]1\[CH2:9][CH2:10][CH2:11][CH2:12][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][C:7]\1=2Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of (2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-9-ylidene)acetonitrile (2.00 g, 9.38 mmol) in ethanol (10 ml) were added a saturated solution of ammonia/ethanol (5 ml) and Raney nickel (W-2, 2 g). The mixture was stirred for 4 hours at 50° C. under hydrogen atmosphere (4 kgf/cm2). The Raney nickel was filtered off, then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (chloroform:methanol=9:1 to chloroform:methanol:triethylamine=90:8:2) to give the above-titled compound (1.50 g, yield 74%, oil).
Workup
- filtrationThe Raney nickel was filtered off
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by means of a silica gel column chromatography (chloroform:methanol=9:1 to chloroform:methanol:triethylamine=90:8:2)
Sources & evidence
- ORD record
- ord-7cd91cb6407147138f1edba48cc20aa9
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235789B1
Reaction notes
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