HCID 53748875, compound → HCID 13827307, compound

HRID 978647Notes

Reaction equation

HRID 978647 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[NH:14][N:13]=[CH:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CN(C)C=O.[Pd]>[CH2:8]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][N:13]=[CH:12]2)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 53748875HCID 53748875, compound

Product 1

HCID 13827307HCID 13827307, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A slurry of 11.2 gm 6-(2-phenylethenyl)-1(2H)-phthalazinone, from the previous example, in 115 ml dimethylformamide was hydrogenated with 1.0 gm 10% palladium on carbon catalyst at 50 psig for 3 hours. The catalyst was filtered off and rinsed with a little dimethylformamide. The filtrate was added to 5 volumes of water, stirred for a few minutes, filtered, washed with water and air dried. Wt=7.8 gm, m.p.=190°-193°. After recrystallization from 80 ml n-butanol the product weighed 6.4 gm and melted at 192°-193°.

Workup

  1. filtrationThe catalyst was filtered off
  2. washrinsed with a little dimethylformamide
  3. additionThe filtrate was added to 5 volumes of water
  4. filtrationfiltered
  5. washwashed with water and air
  6. customdried
  7. customAfter recrystallization from 80 ml n-butanol the product

Sources & evidence

ORD record
ord-ec35ea7bacf949a19bafa0894851898b
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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