1,2,3,4-Tetrahydroisoquinoline → 1,2,3,4-Tetrahydro-7-nitroisoquinoline

HRID 729233Notes

Reaction equation

HRID 729233 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[N+:11]([O-])([O-:13])=[O:12].[K+]>S(=O)(=O)(O)O>[N+:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][NH:2][CH2:1]2)=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 24434Potassium Nitrate

Product 1

HCID 64248331,2,3,4-Tetrahydro-7-nitroisoquinolineYield 50%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

This example shows how to make example compounds of the present invention. More specifically, this example demonstrates how to make four aromatic nitro isomers of 6-position nitro-1,2,3,4-tetrahydroisoquinolinylpurine ribosides NBMPR analogues (compounds 2-5). Several literature methods are employed to synthesize the required nitro-1,2,3,4-tetrahydroisoquinoline (compounds 6-9), which are subsequently reacted with the commercially available 6-chloropurine riboside (10) according to Scheme 1 to obtain the target compounds. The commercially available 5-nitroisoquinoline (11) is reduced using sodium borohydride in ethanol to afford the 5-tetrahydroisoquinoline (6) intermediate in good yield (about 90%). The 7-nitrotetrahydroisoquinoline intermediate (8) is prepared in about 50% yield by nitration of the commercially available 1,2,3,4-tetrahydroisoquinoline using KNO3 in concentrated sulfuric acid according to the method of Ajao et al. (1985) (Scheme 3). The 6- and 8-nitro-1,2,3,4-tetrahydroisoquinoline intermediates 7 and 9, are prepared following reaction Scheme 4 according to the report by Tercel et al. (1996) as follows.

Workup

  1. customin good yield (about 90%)
  2. customreaction Scheme 4 according to the report by Tercel et al. (1996)

Sources & evidence

ORD record
ord-1751e02448a945dbabf83a108c0ad625
Source dataset
uspto-grants-2009_09
Patent number
US07582616B2

Reaction notes

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