HCID 66675967, compound → HCID 59726021, compound

HRID 422575Notes

Reaction equation

HRID 422575 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12](=[O:14])[CH3:13])=[N:7][N:6]=[CH:5]2.[CH3:15][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])([CH3:15])[CH3:13])=[N:7][N:6]=[CH:5]2

Participants

4

Reactant 2

HCID 66675967HCID 66675967, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 59726021HCID 59726021, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(6-chlorophthalazin-1-yl)ethanone (350 mg, 1.69 mmol) in 20 mL of THF at 0° C. was treated with 0.8 mL MeMgBr (3.16 M in Et2O) and stirred at 0° C. for 1 h. The mixture was quenched with saturated NH4Cl, and extracted 2×20 mL EtOAc. The combined EtOAc layers were dried over MgSO4, filtered and concentrated. Purification on an ISCO (12 g column, 15-50% EtOAc:Hexanes) afforded 2-(6-chlorophthalazin-1-yl)propan-2-ol (172 mg, 46% yield) as a pale yellow amorphous solid. MS (ESI, pos. ion) m/z: 223.1 (M+1).

Workup

  1. customThe mixture was quenched with saturated NH4Cl
  2. extractionextracted 2×20 mL EtOAc
  3. dry with materialThe combined EtOAc layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on an ISCO (12 g column, 15-50% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-b392a16b4a9549e6a9d165f440b8f7ba
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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