반응 #81546

반응 방정식

monomethyl terephthalate

4,4-dimethyl-7-amino-1-tetralone

HCl

→

title compound

4-[[(5,6,7,8-Tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)amino]carbonyl]benzoic acid methyl ester

용매

thionylchloride

반응 조건

후처리

1. 1
   농축was then concentrated in vacuo
2. 2
   추출It was extracted with ethyl acetate
3. 3
   세척washed with 1N HCl (4×200 mL)
4. 4
   세척washed with saturated sodium bicarbonate (2×200 mL)
5. 5
   기타The organic phase was then separated
6. 6
   건조dried over magnesium sulfate
7. 7
   농축concentrated in vacuo

실험 절차

A solution of monomethyl terephthalate (VIIIa) (2.86 g, 15.89 mmoles) in thionylchloride (50 mL) with 2 drops of N,N-dimethylformamide was allowed to stir at room temperature. The mixture became homogeneous within 30 minutes and was then concentrated in vacuo. The residue was then taken up in 30 mL of anhydrous pyridine and treated with 4,4-dimethyl-7-amino-1-tetralone (3.00 g, 15.9 mmoles). After 16 hours at room temperature 1N HCl was added to the mixture. It was extracted with ethyl acetate, washed with 1N HCl (4×200 mL) and washed with saturated sodium bicarbonate (2×200 mL). The organic phase was then separated, dried over magnesium sulfate, and concentrated in vacuo to give 5.07 g (Y: 91% ) of the title compound; 1H-NMR (CDCl3): δ8.27 (dd, J=8.7, 2.5 Hz, 1H), 8.19 (bs, 1H), 8.14 (d, J=8.4 Hz, 2H), 7.95 (d, J=8.4 Hz, 2H), 7.91 (d, J=2.5 Hz, 1H), 7.46 (d, J=8.7 Hz, 1H), 3.94 (s, 3H), 2.70 (t, J=7.0 Hz, 3H), 2.00 (t, J=7.0 Hz, 3H), 1.38 (s, 6H); MS (DCI) m/e: 352 (MH+).

출처