TERT-BUTYL 6-HYDROXY-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE synthesis
- Product Name:TERT-BUTYL 6-HYDROXY-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE
- CAS Number:327044-56-4
- Molecular formula:C14H19NO3
- Molecular Weight:249.31
3373-00-0
24424-99-5
327044-56-4
Method E: 6-Hydroxy-1,2,3,4-tetrahydroquinoline (25 g, 172.9 mmol) was dissolved in a solvent mixture of dioxane (200 mL) and 1N NaOH aqueous solution (200 mL), followed by addition of di-tert-butyl dicarbonate (56.6 g, 259.4 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate (2 x 200 mL). The organic layers were combined, washed with saturated saline (1 × 200 mL) and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to give the crude product. The target product tert-butyl 6-hydroxy-3,4-dihydro-2H-quinoline-1-carboxylate (33.0 g, 76.7% yield) was purified by fast column chromatography (Biotage system, eluent: 10% ethyl acetate/hexane).
3373-00-0
136 suppliers
$13.00/250mg
24424-99-5
858 suppliers
$13.50/25G
327044-56-4
52 suppliers
$79.00/100mg
Yield:327044-56-4 93.8%
Reaction Conditions:
in dichloromethane at 50;Sealed tube;
Steps:
tert-butyl-6-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate(K1).
1,2,3,4-tetrahydroquinolin-6-ol(K0) (1 g, 6.7 mmol, 1 eq) andDi-tert-butyl decarbonate (1.68 g, 7.7 mmol, 1.1 eq) were dissolvedin DCM (25 mL) and added into tube sealing. Then reaction mixturewas heated to 50 C. After stirring for 6 h, the solvent was removedunder vacuum. Then the reaction mixture was extracted by EtOAcand washed twice with saturated aqueous NaCl, the organic phasewas dried over anhydrous Na2SO4 and evaporated in vacuum. Thecrude product was purified by column chromatography (PE:EA 8: 1) to get K1 (colorless oil, 1.5 g, 93.8% yield). 1H NMR(400 MHz, DMSO-d6) d ppm 9.09 (s, 1H), 7.29 (d, J 8.8 Hz, 1H), 6.52(dd, J 8.8, 2.9 Hz, 1H), 6.48 (d, J 2.8 Hz, 1H), 3.56 (t, J 6.6 Hz,2H), 2.63 (t, J 6.6 Hz, 2H), 1.77 (p, J 6.5 Hz, 2H), 1.43 (s, 9H).HRMS (DART-TOF) calculated for C14H19NO3 [M Na] 272.1257found 272.1263.
References:
Pu, Chunlan;Tong, Yu;Liu, Yuanyuan;Lan, Suke;Wang, Shirui;Yan, Guoyi;Zhang, Hongjia;Luo, Dan;Ma, Xinyu;Yu, Su;Huang, Qing;Deng, Rui;Li, Rui [European Journal of Medicinal Chemistry,2022,vol. 236,art. no. 114321]
5263-87-6
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$15.00/5g
327044-56-4
52 suppliers
$79.00/100mg
120-15-0
106 suppliers
$12.00/100mg
327044-56-4
52 suppliers
$79.00/100mg