Phthalide → 2-(3-Nitrophenyl)-1H-indene-1,3(2H)-dione

HRID 459746Notes

Reaction equation

HRID 459746 reaction equation
C[O-].[Na+].[C:4]1([C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][O:6]1)=[O:5].[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15].C(OCC)(=O)CC>O.CO>[N+:14]([C:17]1[CH:18]=[C:19]([CH:20]2[C:4](=[O:5])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:6])[CH:22]=[CH:23][CH:24]=1)([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 6885PhthalideHCID 74493-NitrobenzaldehydeHCID 7749Ethyl PropionateHCID 10942334Sodium Methoxide

Product 1

HCID 123282872-(3-Nitrophenyl)-1H-indene-1,3(2H)-dioneYield 65.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium methoxide solution (27% in methanol, 400 g, 2 mol) was added over 40 minutes at 20–30° C. to a stirred mixture of phthalide (67 g, 0.5 mol), 3-nitrobenzaldehyde (75.5 g, 0.5 mol), ethyl propionate (250 ml) and methanol (150 ml). The mixture was stirred at ambient temperature for 15 minutes then it was heated under reflux for 2.5 hours, cooled to ambient temperature and poured into water (2300 ml). The aqueous mixture was washed with ether (5×500 ml) then acetic acid (60 ml) was added. The resulting solid was collected by filtration, washed with water (200 ml) and dried in vacuo to give 2-(3-nitrophenyl)indan-1,3-dione (87.92 g) as a dark red-brown solid, m.pt. 216–226° C., which was used without further purification.

Workup

  1. temperatureit was heated
  2. temperatureunder reflux for 2.5 hours
  3. temperaturecooled to ambient temperature
  4. washThe aqueous mixture was washed with ether (5×500 ml)
  5. additionacetic acid (60 ml) was added
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water (200 ml)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-7cd71b324d8b4c6b9cbabe67c994ea4c
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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