Phthalic Anhydride → 4-(1-Phthalimidoethyl)toluene

HRID 745247Notes

Reaction equation

HRID 745247 reaction equation
[NH2:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)[CH3:3].[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12>>[C:11]1(=[O:16])[N:1]([CH:2]([C:4]2[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=2)[CH3:3])[C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12

Participants

3

Reactant 2

HCID 6811Phthalic AnhydrideHCID 5773861-(4-Methylphenyl)ethanamine

Product 1

HCID 136553264-(1-Phthalimidoethyl)tolueneYield 55.8%

Procedure

A mixture of 9.2 g of 4-(1-aminoethyl)toluene and 10 g of phthalic anhydride was stirred at 145° to 150° C. for 30 minutes. The reaction mixture was purified by silica gel column chromatography (eluted with benzene) to yield 10 g of 4-(1-phthalimidoethyl)toluene; m.p. 65°-66° C.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (eluted with benzene)

Sources & evidence

ORD record
ord-f5894887d90948cda34f9496c3dad1f9
Source dataset
uspto-grants-1986_07
Patent number
US04598077

Reaction notes

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