Ethanol → HCID 19077342, compound

HRID 963648Notes

Reaction equation

HRID 963648 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-3a357a9dbc0e421da3e594e8c042016f
Source dataset
uspto-grants-1998_06
Patent number
US05763611

Reaction notes

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