Dimethylformamide → 4-Phenoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21079

Reaction equation

HRID 21079 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[C:11]([NH:13][C:14]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(CCN(C)C)C.C([Li])(CC)C.CCCCCC.CN([CH:48]=[O:49])C>C1COCC1>[O:1]([C:8]1[CH:25]=[CH:24][CH:23]=[C:10]2[C:9]=1[CH:48]([OH:49])[N:13]([C:14]([CH3:15])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:22])[C:11]2=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684905923-phenoxy-N-(1-methyl-1-phenylethyl)benzamideHCID 178444656HCID 178444656, compound

Product 1

HCID 684884714-Phenoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinoneYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Example 16, 3-phenoxy-N-(1-methyl-1-phenylethyl)benzamide (4.00 g, 12.1 mmol) was dissolved in THF (160 mL), and the solution was treated with TMEDA (5.80 mL, 38.7 mmol), sec-butyllithium-hexane solution (0.99 mol/L, 39.0 mL, 38.7 mmol) and DMF (2.10 mL, 26.6 mmol), followed by purification by slurry using diisopropylether to obtain 4-phenoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (3.92 g, yield 90%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-4874deb46f9647a5996b4bb427bfdff0
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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