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 326438

Reaction equation

HRID 326438 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

4

Reactant 2

HCID 617192Indane-1,3-dione, 2-(3-hydroxyphenyl)-HCID 200923314-Amino-3,5-dimethylphenyltartronic acid

Product 1

HCID 200923526-(1,3-Dioxoindan-2-ylidene)-2-oxo-3-(4-amino-3,5-dimethylphenyl)-2,6-dihydrobenzofuranYield 38%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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)=656nm.

Workup

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

Sources & evidence

ORD record
ord-c3c6f2fe10d64a5db16f7edfb37b40f6
Source dataset
uspto-grants-1993_12
Patent number
US05268490

Linked notes

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