4-chlorophthalazin-1(2H)-one → 4-(4-chlorobenzyl)phthalazin-1(2H)-one

HRID 469637Notes

Reaction equation

HRID 469637 reaction equation
[Cl-].[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Zn+])=[CH:5][CH:4]=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[NH:14][N:13]=1>C1COCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[NH:14][N:13]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 27751424-chlorophthalazin-1(2H)-oneHCID 178478120HCID 178478120, compound

Product 1

HCID 1044524-(4-chlorobenzyl)phthalazin-1(2H)-one

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (4-chlorobenzyl)zinc(II) chloride in THF was added to a suspension of 4-chlorophthalazin-1(2H)-one and Pd(PPh3)4 in THF, and subjected to microwave conditions at 180° C. for 20 minutes. The mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated to give crude 4-(4-chlorobenzyl)phthalazin-1(2H)-one. This material was treated with O-(diphenylphosphoryl)hydroxylamine similar to that described in Example 1B to give the title compound. LC/MS (APCI) M/Z 286 (M+H)+.

Workup

  1. customat 180° C.
  2. customfor 20 minutes
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c48463139c604ffaad438ceff0c315a4
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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