Benzene → 2,4-Bis(1-n-propyl-2-methyl-3-indolyl)-4-oxobutanoic acid

HRID 616786Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:11]1(=[O:17])[O:16][C:14](=[O:15])[CH:13]=[CH:12]1.[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)(=O)C>[CH2:7]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH:12]([CH2:13][C:14]([C:1]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:3]([CH2:4][CH2:5][CH3:6])[C:2]=2[CH3:10])=[O:15])[C:11]([OH:16])=[O:17])=[C:2]1[CH3:1])[CH2:8][CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred solution of 90.0 g (0.686 mole) of 2-methylindole, 30.0 g (0.306 mole) of maleic anhydride, 350 ml of benzene and 5.0 ml of glacial acetic acid was heated at reflux under a nitrogen atmosphere for a period of approximately sixty-five hours. The resulting slurry was cooled to approximately 60° C and the solid was collected by filtration, washed with approximately 100 ml of benzene that had been heated to approximately 60° C. After drying to a constant weight of 29.7 g in vacuo at 60° C there was obtained 2,4-bis(2-methyl-3-indolyl)-4-oxobutanoic acid (Formula VII: R=Y=H; R1 =CH3) as a pale yellow solid which melted at 217°-218° C with decomposition.

Workup

temperatureat reflux under a nitrogen atmosphere for a period of approximately sixty-five hours
filtrationthe solid was collected by filtration
washwashed with approximately 100 ml of benzene that
temperaturehad been heated to approximately 60° C
customAfter drying to a constant weight of 29.7 g in vacuo at 60° C

Sources & evidence

ORD record: ord-7fb0963110f8437d85b1f8eafbc09bae
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04075224

Reaction notes

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