Phosphate → HCID 14567294, compound

HRID 443380Notes

Reaction equation

HRID 443380 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[C:10]([C:11]=1[CH:12]=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.P([O-])([O-])([O-])=[O:21].[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[C:10]([C:11]=1[C:12]([OH:21])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 1061PhosphateHCID 516875Potassium PermanganateHCID 145672483-Chloro-1-phenylisoquinoline-4-carbaldehyde

Product 1

HCID 14567294HCID 14567294, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

53.5 g 3-Chloro-1-phenyl-isoquinoline-4-aldehyde are suspended in 1.5 l of acetone and 500 ml of phosphate buffer of pH 7. At 40° C., 40 g of potassium permanganate are introduced portionwise within 2 hours and stirring is continued at this temperature for 2 hours. The excess potassium permanganate is destroyed with 10 g sodium hydrogenosulfite and the solution is concentrated to 500 ml and filtered. The filtrate is brought to pH 4 with concentrated hydrochloric acid followed by thorough extraction with acetic ester. Removal of the solvent in vacuo provides 41.1 g of 3-chloro-1-phenyl-isoquinoline-4 carboxylic acid having a melting point of 208° C.

Workup

  1. customThe excess potassium permanganate is destroyed with 10 g sodium hydrogenosulfite
  2. concentrationthe solution is concentrated to 500 ml
  3. filtrationfiltered
  4. extractionfollowed by thorough extraction with acetic ester
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-7d023e8192de49ca9356f754fa684acb
Source dataset
uspto-grants-1981_04
Patent number
US04260611

Reaction notes

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