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65242-27-5

2-CHLORO-5,6,7,8-TETRAHYDROQUINOLINE-3-CARBONITRILE synthesis

3synthesis methods
4241-13-8 Synthesis
2-OXO-1,2,5,6,7,8-HEXAHYDRO-3-QUINOLINECARBONITRILE

4241-13-8
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Yield:65242-27-5 99%

Reaction Conditions:

with trichlorophosphate at 100; for 12 h;

Steps:

10.3 Step 3: 2-Chloro-5,6, 7,8-tetrahydroquinoline-3-carbonitrile

A solution of 2-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile (2 g, 11.48 mmol) in POCh (17.60 g, 114.81 mmol) was stirred at 100 °C for 12 hrs. The mixture was concentrated to give a residue. The residue was adjusted to pH=8 with 2 M aqueous NaOH and extracted with EtOAc (3x). The combined organic layers were dried over Na2SO4, filtered and concentrated to afford the title compound (2 g, 99%) as a yellow solid which was used without further purification. JH NMR (400MHz, DMSO-de) 8 8.17 (s, 1H), 2.93 - 2.69 (m, 4H), 1.87 - 1.66 (m, 4H). MS-ESI (m/z) calc’d for C10H10CIN2 [M+H]+: 193.1. Found 193.1.

References:

WO2022/155419,2022,A1 Location in patent:Page/Page column 127-129