ChemicalBook CAS DataBase List 7-NITRO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE

7-NITRO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE synthesis

10synthesis methods

Product Name:7-NITRO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
CAS Number:42923-79-5
Molecular formula:C9H10N2O2
Molecular Weight:178.19

91-21-4
256 suppliers
$5.00/5g

42923-79-5
124 suppliers
$15.00/250mg

Yield:42923-79-5 86%

Reaction Conditions:

with sodium nitrate;sulfuric acid at 4 - 20; for 16 h;

Steps:

5 2-Allyl- 1 -(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-((2-methyl- 1,2,3 ,4-tetrahydroisoquinolin-7-yl)amino)- 1 ,2-dihydro-3H-pyrazolo[3 ,4-d]pyrimidin-3-one

To concentrated H2504 solution (62 mL) at 4 °C was added 1,2,3,4- tetrahydroisoquinoline (15 g, 112.78 mmol) dropwise keeping the temperature below 15 °C. To the stifling mixture at 4 °C was added NaNO3 (12.5, 148.80 mmol) keeping internal temperature below 10 °C. The reaction mixture was stined at RT for 16 h. The reaction mixture was added to NH4OH (185 mL) to a final pH = 8. The mixture was extracted with DCM (3 x 150 mL), washed with brine (75 mL) and dried (Na2504). The solvent was removed. The resulting crude was dissolved in EtOH (50 mL) and concentrated HC1 (14 mL) was added. The resulting solid was filtered and washed with diethyl ether to afford 7-nitro- 1,2,3,4-tetrahydroisoquinoline (13 g, 86%) as a mixture of isomers. MS (ESI) mlz: 179.1 [M+H].

References:

WO2019/28008,2019,A1 Location in patent:Paragraph 0141