Ethanol → HCID 19077342, compound

HRID 275026Notes

Reaction equation

HRID 275026 reaction equation
[ClH:1].[NH2:2][C:3]1[C:4]([OH:13])=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[N:10][CH:9]=[CH:8]2.C(O[N:19]=O)(C)(C)C.C(O)C>O>[Cl-:1].[OH:13][C:4]1[C:3]([N+:2]#[N:19])=[C:12]2[C:7]([CH:8]=[CH:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 10906Tert-Butyl nitriteHCID 67670050HCID 67670050, compound

Product 1

HCID 19077342HCID 19077342, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 8-amino-7-hydroxyisoquinoline HCl salt (4.94 g, 0.025 mol) in ethanolic-HCl at 0° C. is added dropwise a solution of tert-butylnitrite (17.46 ml), ethanol (790 ml) and water (58 ml). Following completion of the addition, the solution is stirred an additional 2 hours at 0° C. The product is precipitated from the reaction mixture by the addition of diethyl ether (2 l). The product is collected by filtration and rinsed with diethyl ether to provide the desired product (2.6 g) in 50% yield.

Workup

  1. additioncompletion of the addition
  2. customThe product is precipitated from the reaction mixture by the addition of diethyl ether (2 l)
  3. filtrationThe product is collected by filtration
  4. washrinsed with diethyl ether

Sources & evidence

ORD record
ord-f606b87b0897485ba8455892cb5d553f
Source dataset
uspto-grants-1995_02
Patent number
US05391743

Reaction notes

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