Phthalide → HCID 25131904, compound

HRID 1402974Notes

Reaction equation

HRID 1402974 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].[CH:14]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20])=O.C(OCC)(=O)CC>CO>[O:5]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:6])[CH:14]1[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20]

Participants

6

Reactant 4

HCID 6885PhthalideHCID 7749Ethyl PropionateHCID 90670m-FormylbenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 25131904HCID 25131904, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 27% sodium methoxide solution in methanol (400 g, 2 mol) and methanol (150 ml) was added dropwise between ambient temperature and 30° C. over 15 minutes to a stirred mixture of phthalide (67 g, 0.5 mol), 3-formylbenzonitrile (65.5 g, 0.5 mol) and ethyl propionate (250 ml), the mixture was stirred at ambient temperature for 40 minutes and at reflux temperature for 1 hour, then it was allowed to cool to ambient temperature. The resulting red solid was collected by filtration, washed with ethyl acetate (2×50 ml) and dissolved in water (1800 ml). The solution was acidified by the addition of acetic acid (60 ml) and the resulting red solid was collected by filtration, washed with water (2×200 ml) and dried in vacuo to give 3-(1,3-dioxoindan-2-yl)benzonitrile (83.2 g) as a dark red solid, m.pt. 179-182° C., m/z (M+H)+. 248, which was used without further purification.

Workup

  1. temperatureat reflux temperature for 1 hour
  2. temperatureto cool to ambient temperature
  3. filtrationThe resulting red solid was collected by filtration
  4. washwashed with ethyl acetate (2×50 ml)
  5. dissolutiondissolved in water (1800 ml)
  6. additionThe solution was acidified by the addition of acetic acid (60 ml)
  7. filtrationthe resulting red solid was collected by filtration
  8. washwashed with water (2×200 ml)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-c9c7aa125fca46539360b774e5b36649
Source dataset
uspto-grants-2014_12
Patent number
US08912187B2

Reaction notes

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