Indane-1,3-dione, 2-(3-hydroxyphenyl)- → 6-(1,3-Dioxoindan-2-ylidene)-2-oxo-3-(4-amino-3,5-dimethylphenyl)-2,6-dihydrobenzofuran

HRID 274215Notes

Reaction equation

[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([C:14](O)=O)(O)[C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[CH3:17].O[C:19]1[CH:20]=[C:21]([CH:25]2[C:33](=[O:34])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:35])[CH:22]=[CH:23]C=1>C(O)(=O)C>[O:34]=[C:33]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:35])[C:25]1=[C:21]1[CH:22]=[CH:23][C:14]2=[C:9]([C:5]3[CH:4]=[C:3]([CH3:17])[C:2]([NH2:1])=[C:7]([CH3:8])[CH:6]=3)[C:10](=[O:11])[O:12][C:19]2=[CH:20]1

Participants

Conditions

Temperature: 20 °C

Procedure

4-Amino-3,5-dimethylphenyltartronic acid (2.1 parts), 2-(3-hydroxyphenyl)-1,3-indandione (1.3 parts) and glacial acetic acid (125 parts) were stirred under reflux for 2 hours. The reaction mixture was cooled to 20° C. and the precipitated solid was recovered by filtration, washed with methanol and dried to give 6-(1,3-dioxoindan-2-ylidene)-2-oxo-3-(4-amino-3,5-dimethylphenyl)-2,6-dihydrobenzofuran (0.9 parts, 38%), m.pt. >250° C. λmax (CH2Cl2)=656 nm.

Workup

temperatureunder reflux for 2 hours
filtrationthe precipitated solid was recovered by filtration
washwashed with methanol
customdried

Sources & evidence

ORD record: ord-0ec80b141a614a3b9733eca5480e2feb
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05389597

Reaction notes

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