3-Nitrophthalic acid → 2-[4-(1,1-Dimethylethyl)phenyl]-4-nitro-1H-isoindole-1,3(2H)-dione

HRID 2251873Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]=1[C:13]([OH:15])=O)([O-:3])=[O:2].[C:16]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>ClC1C=CC=CC=1Cl>[C:16]([C:20]1[CH:21]=[CH:22][C:23]([N:24]2[C:13](=[O:15])[C:5]3[C:6](=[CH:10][CH:11]=[CH:12][C:4]=3[N+:1]([O-:3])=[O:2])[C:7]2=[O:9])=[CH:25][CH:26]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 150 °C

Procedure

In a 25 mL round bottomed flask, 3-nitrophthalic acid (1 g, 4.7 mmol) was suspended in 1,2-dichlorobenzene (3 mL). To this was added 4-tert-butylaniline (3 mL, 18.8 mmol). The reaction was heated to 150° C., resulting in a blood red solution. The reaction was held at 150° C. for 2.5 h, then poured into a 125 mL Erlenmeyer flask. Precipitation began to occur and 50 mL of Et2O was added to the flask. The suspension was stirred for 15 h and filtered. The filtered cake was washed copiously with Et2O and dried in vacuo at 30° C. for 4 h to afford a white brittle powder. No further purification was performed on this compound. MS (ES+): 325.1(M+H)+. Calc'd for C18H16N2O4-324.33.

Workup

customresulting in a blood red solution
additionpoured into a 125 mL Erlenmeyer flask
customPrecipitation
addition50 mL of Et2O was added to the flask
filtrationfiltered
washThe filtered cake was washed copiously with Et2O
customdried in vacuo at 30° C. for 4 h
customto afford a white brittle powder
customNo further purification

Sources & evidence

ORD record: ord-094b965d91cb4ebb9b197cbd01126dc0
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320992B2

Reaction notes

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