Sodium → 1,3-Dioxo-2,3-dihydro-1H-indene-2-carbonitrile

HRID 596891Notes

Reaction equation

HRID 596891 reaction equation
[C:1]([CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])[O:5]1)#[N:2].[Na]>CO>[C:1]([CH:3]1[C:6](=[O:7])[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]1=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 54508334HCID 54508334, compound

Product 1

HCID 2945201,3-Dioxo-2,3-dihydro-1H-indene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Cyanomethylene phthalide (6.0 g.; 0.035 mole) was added to a solution of sodium (0.8 g.) in methanol (35 ml) and the red solution refluxed for 20 mins. On cooling and acidification with one-third of its bulk of concentrated hydrochloric acid the indandione separated as a copious yellow solid, m.p. 204°-207° C (d) (lit. m.p. 201°-202° C).

Workup

  1. temperaturethe red solution refluxed for 20 mins
  2. temperatureOn cooling
  3. customacidification with one-third of its bulk of concentrated hydrochloric acid the indandione separated as a copious yellow solid, m.p. 204°-207° C (d) (lit. m.p. 201°-202° C)

Sources & evidence

ORD record
ord-3ef5616c28b9452fb2e038713ee4e1d0
Source dataset
uspto-grants-1977_03
Patent number
US04012407

Reaction notes

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