HCID 178418361, compound → HCID 178486675, compound

HRID 986639Notes

Reaction equation

HRID 986639 reaction equation
[OH:1][C:2]1[N:3]=[C:4]([CH3:19])[C:5]2[C:10]([C:11]=1[N+:12]([O-])=O)=[CH:9][C:8]([O:15][CH3:16])=[C:7]([O:17][CH3:18])[CH:6]=2.[H][H]>C(OC(=O)C)(=O)C.C(O)(=O)C.[Pd]>[OH2:1].[C:2]([NH:12][C:11]1[C:10]2[C:5](=[CH:6][C:7]([O:17][CH3:18])=[C:8]([O:15][CH3:16])[CH:9]=2)[C:4]([CH3:19])=[N:3][C:2]=1[OH:1])(=[O:1])[CH3:11].[C:8]([NH:12][C:11]1[C:10]2[C:5](=[CH:6][C:7]([O:17][CH3:18])=[C:8]([O:15][CH3:16])[CH:9]=2)[C:4]([CH3:19])=[N:3][C:2]=1[OH:1])(=[O:15])[CH3:7]

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178486677HCID 178486677, compound

Product 1

HCID 178486675HCID 178486675, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A slurry of 2.028 grams 3-hydroxy-6,7-dimethoxy-1-methyl-4-nitroisoquinoline (BA) (7.67 mmol) in 28 ml acetic anhydride and 180 ml acetic acid was hydrogenated using 0.8 grams of a 10% palladium on carbon catalyst at 25 psi hydrogen pressure in a Parr hydrogenator for 3 hours. The mixture was filtered through a Celite pad, and the collected solids were washed with acetic acid. The filtrate and the wash liquids were combined and evaporated to dryness. The residue was recrystallized from methanol to provide 0.70 grams of Compound BG (33% yield) having a melting point of >300° C. (with decomposition).

Workup

  1. customfor 3 hours
  2. filtrationThe mixture was filtered through a Celite pad
  3. washthe collected solids were washed with acetic acid
  4. customevaporated to dryness
  5. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-d2f34ae41d82493a890ede01d7a5ff2f
Source dataset
uspto-grants-1987_12
Patent number
US04714705

Reaction notes

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