Sodium Methoxide → 5,6-Diethyl-1,3-dioxo-2,3-dihydro-1H-indene-2-carbonitrile

HRID 437846Notes

Reaction equation

HRID 437846 reaction equation
[C:1]([CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:16][CH3:17])=[C:11]([CH2:14][CH3:15])[CH:12]=2)[C:6](=[O:7])[O:5]1)#[N:2].C[O-].[Na+]>Cl>[C:1]([CH:3]1[C:6](=[O:7])[C:8]2[C:13](=[CH:12][C:11]([CH2:14][CH3:15])=[C:10]([CH2:16][CH3:17])[CH:9]=2)[C:4]1=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54399111(5,6-Diethyl-3-oxo-2-benzofuran-1(3H)-ylidene)acetonitrile

Product 1

HCID 123664115,6-Diethyl-1,3-dioxo-2,3-dihydro-1H-indene-2-carbonitrileYield 79%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-cyanomethylene-5,6-diethylphthalide (4.7 g; 0.021 mole) and methanolic sodium methoxide (from sodium [0.48 g] and methanol [21 ml]) was refluxed for 20 mins., cooled, and the red solution poured into 5N hydrochloric acid (100 ml). The precipitated yellow solid was filtered off and dried in vacuo over P2O5 /NaOH to yield 3.711 g (79%) of material of m.p. 172°-173° C. (d). (Found; C, 73.60; H, 5.94; N, 6.13; C14H13NO2 requires; C, 73.99; H, 5.77; N, 6.16%).

Workup

  1. temperaturewas refluxed for 20 mins
  2. temperature, cooled
  3. filtrationThe precipitated yellow solid was filtered off
  4. dry with materialdried in vacuo over P2O5 /NaOH

Sources & evidence

ORD record
ord-f80d5bb6723f4b9a9c27fa21b02fe540
Source dataset
uspto-grants-1977_06
Patent number
US04032544

Reaction notes

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