Dimethylformamide → HCID 19777595, compound
Reaction equation
Cl[CH:2](OCC)[CH:3]([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[CH2:13](N)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C[N:28](C)C=O>>[CH2:13]([C:2](=[NH:28])[CH:3]([O:4][CH2:5][CH3:6])[O:7][CH2:8][CH3:9])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
Procedure
A mixture of 158 mg (0.80 mmole) of 1-chloro-1,2,2-triethoxyethane (produced in accordance with Example IV), 0.10 mL (0.92 mmole) of benzylamine, and 136 mg (0.985 mmole) of anhydrous potassium carbonate in 1.00 mL of dimethylform-amide, spectrophotometric-grade, commercially available from Aldrich Chemical Co., Milwaukee, Wis., was stirred, while being protected from atmospheric moisture, at 0° C. for 45 minutes. Isolation of the product as described in the procedure of Example XVII afforded 146 mg (82% yield) of the title compound, whose IR and proton NMR spectral properties were consistent with the assigned structure. This transformation should prove to be quite useful for an industrial-scale synthesis of isoquinoline, previously prepared in high yield by treatment of the named imine with aqueous acid. Unfortunately, the reported preparation of this imine required using glyoxal monoacetal derivatives which are susceptible to polymerization and therefore not easily purified. See: E. Schlittler and J. Muller, Helv. Chim. Acta, 31:914 (1948).
Sources & evidence
- ORD record
- ord-cad76b9015fc4780bad6dcc688c0b46d
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05191127
Reaction notes
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