4-Methoxystyrene → HCID 21293339, compound

HRID 622127Notes

Reaction equation

HRID 622127 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[N:6]=[CH:5]2.Cl.O1CCN(CCCl)CC1.Cl.C(N(C(C)C)CCCl)(C)C.[CH3:42][O:43][C:44]1[CH:51]=[CH:50][C:47]([CH:48]=[CH2:49])=[CH:46][CH:45]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(O)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C.CS(C)=O>[BrH:1].[CH3:42][O:43][C:44]1[CH:51]=[CH:50][C:47](/[CH:48]=[CH:49]/[C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:6]=[CH:5]3)=[CH:46][CH:45]=1

Participants

10

Reactant 5

HCID 125074-MethoxystyreneHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 779422-Chloroethyldiisopropylammonium chlorideHCID 80271Tri-o-tolylphosphineHCID 21293342HCID 21293342, compound

Product 1

HCID 21293339HCID 21293339, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

6-Bromo-2-(2-morpholinoethyl)phthalazin-1(2H)-one (10.1 gm, 0.03 mole) (prepared as in Example I, except that 2-morpholinoethyl chloride hydrochloride was substituted for the 2-(diisopropylamino)ethyl chloride hydrochloride) was stirred into 16 ml DMSO plus 16 ml acetonitrile. To the resulting mixture was added 4.5 gm 4-methoxystyrene (0.033 mole), 0.1 gm tri(o-tolyl)phosphine, and 0.02 gm palladium acetate. The reaction mixture was stirred at reflux (95°-100° C.) for 24 hours. Allowed to cool to about 60° C. and diluted with 60 ml of isopropanol. Stirred for an hour, filtered, washed to colorless washings with isopropanol and dried. The product weighed 11.9 gm. After recrystallization from 40 ml ethanol plus 30 ml water the product weighed 9.2 gm and melted at 254°-256° C.

Workup

  1. temperatureat reflux (95°-100° C.) for 24 hours
  2. stirringStirred for an hour
  3. filtrationfiltered
  4. washwashed
  5. washwashings with isopropanol
  6. customdried
  7. customAfter recrystallization from 40 ml ethanol plus 30 ml water the product

Sources & evidence

ORD record
ord-28db04c7dc4747e68fb433f9a6809516
Source dataset
uspto-grants-1988_09
Patent number
US04769369

Reaction notes

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