2-ACETYL-6,7-DIMETHOXY-1-METHYLENE-1,2,3,4-TETRAHYDROISOQUINOLINE synthesis
- Product Name:2-ACETYL-6,7-DIMETHOXY-1-METHYLENE-1,2,3,4-TETRAHYDROISOQUINOLINE
- CAS Number:57621-04-2
- Molecular formula:C14H17NO3
- Molecular Weight:247.29
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Yield:57621-04-2 88%
Reaction Conditions:
with pyridine in dichloromethane at 60; for 3 h;
Steps:
Procedure for preparation of 1-(6,7-dimethoxy-1-methylene-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (6) (CAS Number: 57621-04-2)
To a round-bottomed flask were added 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline (9) (2.5 mmol, 513 mg) and a mixture of pyridine and acetic anhydride (1:1) (3.6 mL). The round-bottomed flask was capped with a rubber septum and the mixture was stirred at 60 °C for 3 h. Afterwards, the reaction mixture was cooled to room temperature and diluted with dichloromethane (15 mL). The mixture was washed with distilled water (15 mL) and with a 10% (w/v) aqueous solution of NaHCO3 (2 x 15 mL). The organic phase was dried over MgSO4. The residue was purified by column chromatography on silica gel using ethyl acetate as eluent to afford the desired product 6. Yield: 543 mg (88%); off-white solid; m.p. 100-101 oC (lit.15 m.p. 106-107 oC); Rf = 0.48 (eluent: ethyl acetate). 1H NMR (300 MHz, CDCl3): δ 7.08 (s, 1H), 6.59 (s, 1H), 5.60 (s, 1H), 4.97 (s, 1H), 3.98 (t, J = 6.0 Hz, 2H), 3.91 (s, 3H), 3.88 (s, 3H), 2.83 (t, J = 6.0 Hz, 2H), 2.23 (s, 3H); 13C NMR (75 MHz, CDCl3): δ 169.3, 149.7, 147.6, 143.1, 127.9, 123.6, 111.1, 106.6, 104.2, 55.9, 55.8, 41.6, 28.5, 22.3; IR (KBr, cm-1): 3070.7, 2933.7, 1624.1, 1512.2, 1448.5, 1288.5, 974.1, 896.9; GC/MS (m/z, %): 247 (94.7), 232 (10.7), 219 (1.3), 204 (100.0), 190 (44.5) 174 (22.5).
References:
Corrêa, Bianca K.;Silva, Tamiris R.C.;Raminelli, Cristiano [Tetrahedron Letters,2018,vol. 59,# 39,p. 3583 - 3585] Location in patent:supporting information
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