TERT-BUTYL 8-HYDROXY-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE synthesis
- Product Name:TERT-BUTYL 8-HYDROXY-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE
- CAS Number:676255-10-0
- Molecular formula:C14H19NO3
- Molecular Weight:249.31
6640-50-2
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Yield:676255-10-0 84.7%
Reaction Conditions:
with sodium hydroxide in 1,4-dioxane;water at 20;
Steps:
4 Preparation 4; 8-Hydroxy-3, [4-DIHYDRO-2H-QUINOLINE-L-CARBOXYLIC] acid tert-butyl ester;
Procedure G: 1, 2,3, 4-Tetrahydro-quinolin-8-ol (CAS Registry Number 6640-50-2) (25.8 g, 172.9 mmol) is treated with di-tert-butyl dicarbonate (56.6 g, 259.4 mmol) in a solvent mixture of dioxane (200 mL) and IN [NAOH] (200 [ML),] and reaction mixture allowed to stir at room temperature overnight. The layers are separated, and the aqueous layer is washed with ethyl acetate (2X). The organic layers are combined and washed with brine [(1X),] dried over [NA2S04] and the organic layer evaporated to give a crude oil. Flash chromatography (Biotage, 10% EtOAc/hexanes) gives the desired material (36.5 g, 84. 7%). Calculated for [C14H, GN03] : C, 67.44 ; H, 7.68 ; N, 5.62. Found: C, 67.91 ; H, 7.92 ; N, 5.76.
References:
WO2004/26837,2004,A2 Location in patent:Page 24
938-33-0
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53899-17-5
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