4-Methoxystyrene → HCID 21293332, compound

HRID 622126Notes

Reaction equation

HRID 622126 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]([CH3:17])[CH3:16])[N:6]=[CH:5]2.Cl.CN(C)CCCl.Cl.C(N(C(C)C)CCCl)(C)C.[CH3:36][O:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=[CH2:43])=[CH:40][CH:39]=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].[CH3:36][O:37][C:38]1[CH:45]=[CH:44][C:41](/[CH:42]=[CH:43]/[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]([CH3:17])[CH3:16])[N:6]=[CH:5]3)=[CH:40][CH:39]=1

Participants

10

Reactant 5

HCID 125074-MethoxystyreneHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 80271Tri-o-tolylphosphineHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 17846762HCID 17846762, compound

Product 1

HCID 21293332HCID 21293332, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
60 °C

Procedure

6-Bromo-2-[2-(dimethyamino)ethyl]phthalazin-1(2H)-one (7.2 gm, 0.018 mole) (prepared as in Example I, except that 2-(dimethylamino)ethyl 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 10.7 gm. After recrystallization from 240 ml methoxyethanol the product weighed 6.4 gm and melted at 265°-267° 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 240 ml methoxyethanol the product

Sources & evidence

ORD record
ord-4e212aaf2d024257a85b02ab13d8edc1
Source dataset
uspto-grants-1988_09
Patent number
US04769369

Reaction notes

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