6-Bromo-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carbaldehyde synthesis

2synthesis methods

Product Name:6-Bromo-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carbaldehyde
CAS Number:345964-67-2
Molecular formula:C12H14BrNO
Molecular Weight:268.15

6-bromo-1,2,3,4-tetrahydro-4,4-dimethylquinoline hydrochloride

135631-91-3
65 suppliers
$95.00/50mg

6-Bromo-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carbaldehyde

345964-67-2
4 suppliers
inquiry

Yield:345964-67-2 90%

Reaction Conditions:

in formic acid;hexane;

Steps:

6-Bromo-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-1-carbaldehyde (Intermediate 50)

6-Bromo-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-1-carbaldehyde (Intermediate 50) A solution of 6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline, available in accordance with U.S. Pat. No. 5,089,509, the specification of which is incorporated herein by reference (1.8 g, 7.5 mmol) in 10 mL of formic acid was refluxed for 3 h. The reaction mixture was then cooled to ambient temperature and poured into ice-cold saturated aqueous sodium bicarbonate solution and extracted with diethyl ether (*2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was subjected to flash column chromatography over silica gel (230-400 mesh) using 15-25% ethyl acetate in hexane as the eluent to afford the title compound as a pale yellow solid (1.8 g, 90%). ¹H NMR (300 MHz, CDCl₃): δ8.71 (s, 1H), 7.45 (d, 1H, J=2.2 Hz), 7.28 (dd, 1H, J=2.2, 8.5 Hz), 6.98 (d, 1H, J=8.5 Hz), 3.78 (t, 2H, J=6.3 Hz), 1.74 (t, 2H, J=6.3 Hz), 1.28 (s, 6H).

References:

US6313107,2001,B1

64-18-6 Synthesis

64-18-6
1078 suppliers
$22.12/250ML

135631-91-3
65 suppliers
$95.00/50mg

345964-67-2
4 suppliers
inquiry

References