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
133 suppliers
$13.00/250mg
24424-99-5
840 suppliers
$13.50/25G
327044-56-4
46 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
311 suppliers
$15.00/5g
327044-56-4
46 suppliers
$79.00/100mg
120-15-0
98 suppliers
$12.00/100mg
327044-56-4
46 suppliers
$79.00/100mg