N-Methylphthalimide → 2-(2-(4-methoxyphenyl)acetyl)-N-methylbenzamide

HRID 911118Notes

Reaction equation

HRID 911118 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][Mg]Cl)=[CH:5][CH:4]=1.[CH3:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23]>C1COCC1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][C:21]([C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]([NH:13][CH3:12])=[O:23])=[O:22])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 11074N-MethylphthalimideHCID 178490607HCID 178490607, compound

Product 1

HCID 667315312-(2-(4-methoxyphenyl)acetyl)-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., (4-methoxybenzyl)magnesium chloride (0.25 M in THF) (37 ml, 9.3 mmol) was added to 2-methylisoindoline-1,3-dione (1.00 g, 6.2 mmol) in THF (3.0 mL) (Reference: Synthetic Comm. 2004, 34(7), 1301-1308). The mixture was stirred at 0° C. for 5 minutes, then quenched with 10 mL of water. The reaction was warmed to RT and concentrated to yield 2-(2-(4-methoxyphenyl)acetyl)-N-methylbenzamide as a white solid (crude). The material was carried on to next step without further purification. MS m/z=284 [M+1]+. Calc'd for C17H17NO3: 283.33.

Workup

  1. customquenched with 10 mL of water
  2. temperatureThe reaction was warmed to RT
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4894361d65ae44108dc58518afbc6b41
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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