HCID 21293345, compound → HCID 13827309, compound

HRID 978662Notes

Reaction equation

HRID 978662 reaction equation
Cl.[OH:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17](=[O:21])[N:16]([CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[N:15]=[CH:14]3)=[CH:5][CH:4]=1>CO.O.[Pd]>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17](=[O:21])[N:16]([CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[N:15]=[CH:14]3)=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 21293345HCID 21293345, compound

Product 1

HCID 13827309HCID 13827309, compoundYield 94.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Trans-6-[2-(4-Hydroxyphenyl)ethenyl]-2-(3-dimethylaminopropyl)-1(2H)-phthalazinone hydrochloride (5 g) in methanol (100 ml) and water (10 ml) was hydrogenated at 50 psi over 10% Pd/C (0.5 g). After 6 hours the catalyst was filtered and the filtrate was diluted with ether (600 ml). The precipitated product was filtered to give 4.3 g of the saturated product as the hydrochloride mp. 234°-236° C.

Workup

  1. filtrationAfter 6 hours the catalyst was filtered
  2. additionthe filtrate was diluted with ether (600 ml)
  3. filtrationThe precipitated product was filtered

Sources & evidence

ORD record
ord-3bfc97c3099e446fb8b2b8fbd57a4013
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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