Phthalide → HCID 57949759, compound

HRID 2427639Notes

Reaction equation

HRID 2427639 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][O:3]1)=O.[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCCCCC.C(OCC)(=O)C>[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][N:21]2[CH2:1][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:3])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6885PhthalideHCID 83242Benzenebutanamine

Product 1

HCID 57949759HCID 57949759, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of phthalide (0.268 g, 2 mmol) and 4-phenyl-butylamine (0.316 mL, 2 mmol) was stirred at 150° C. for 16 h. Workup and silica gel column chromatography (2:1 hexane-ethyl acetate) afforded 2-(4-phenyl-butyl)-2,3-dihydro-isoindol-1-one (0.055 g, 11%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.70 (m, 4H), 2.71 (t, 2H), 3.66 (t, 2H), 4.31 (s, 2H), 7.14-7.56 (m, 8H), 7.82 (s, 1H).

Sources & evidence

ORD record
ord-353fc50144724dbdab87b494d9b0f86f
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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