3'-Aminoacetophenone → HCID 67338914, compound

HRID 2092350Notes

Reaction equation

HRID 2092350 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([I:13])[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[NH2:14][C:15]1[CH:16]=[C:17]([C:21](=[O:23])[CH3:22])[CH:18]=[CH:19][CH:20]=1.CCOC(C)=O>CC(O)C.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[I:13][C:7]1[C:8]([CH3:12])=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[N:4][N:3]=[C:2]2[NH:14][C:15]1[CH:16]=[C:17]([C:21](=[O:23])[CH3:22])[CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 74173'-AminoacetophenoneHCID 8857Ethyl AcetateHCID 86614221HCID 86614221, compound

Product 1

HCID 67338914HCID 67338914, compoundYield 24.2%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 1-chloro-5-iodo-6-methylphthalazine (0.380 g, 1.25 mmol) in IPA (3.0 ml), charged to a 5 mL microwave reaction vessel, 3′-aminoacetophenone (0.253 g, 1.87 mmol) was added. The reaction mixture was stirred at 160° C. for 15 min. The reaction mixture was diluted with excess DCM and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The resulting residue was loaded on to silica and purified by column chromatgraphy. (ISCO 40.0 g, 10-70% EtOAc in Hex., 25 min.) to give 1-(3-(5-iodo-6-methylphthalazin-1-ylamino)phenyl)ethanone (0.122 g, 24.2% yield). MS (M+H)+ 404.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. custompurified by column chromatgraphy

Sources & evidence

ORD record
ord-5a515755aaab484b838e3511113f87df
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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