Dichloromethane → 5,8-Isoquinolinedione

HRID 1632947Notes

Reaction equation

HRID 1632947 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9](N)=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:14].[K+].[K+].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.C(Cl)Cl>O.S(=O)(=O)(O)O>[CH:7]1[C:8]2[C:9](=[O:14])[CH:10]=[CH:11][C:2](=[O:1])[C:3]=2[CH:4]=[CH:5][N:6]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24502Potassium Dichromate3×HCID 24503Dichromate ionHCID 133746358-Aminoisoquinolin-5-ol

Product 1

HCID 57665,8-Isoquinolinedione

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent3×

Procedure

Nineteen grams of 5-hydroxy-8-amino-isoquinoline were dissolved in 450 ml of water and 10 ml of concentrated sulfuric acid. The solution was cooled in an ice bath and then 50 ml of a potassium dichromate solution were added. (The dichromate solution was made by dissolving 50 g of potassium dichromate in 500 ml of water.) Forty ml of concentrated sulfuric acid were added, followed by 190 ml of the potassium dichromate solution, then 20 ml of concentrated sulfuric acid, and finally 400 ml of methylene chloride.

Workup

  1. temperatureThe solution was cooled in an ice bath

Sources & evidence

ORD record
ord-3351e62c0a4a4870a9dc075c5b712179
Source dataset
uspto-grants-1984_10
Patent number
US04478820

Reaction notes

Loading…