1-Oxo-2,3-Dihydro-1H-Indene-4-Carbonitrile → 5-Oxo-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

HRID 1684331Notes

Reaction equation

HRID 1684331 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12])#[N:2].[C:13](=O)(O)O.NNC(N)=N>CO.O.Cl>[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:13][CH2:5][CH2:6][C:7]2=[O:12])#[N:2]

Participants

6

Reactant 2

HCID 27515831-Oxo-2,3-Dihydro-1H-Indene-4-CarbonitrileHCID 178513185HCID 178513185, compound

Product 1

HCID 109318735-Oxo-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-Cyano-1-indanone-2'-amidinohydrazone hydrochloride Analogously to Example 1,314 mg (2 mmol) of 4-cyano-1-indanone are dissolved in 20 ml of methanol; a solution of 272 mg (2 mmol) of aminoguanidine hydrogen carbonate in 9 ml of water and 1 ml of 2N hydrochloric acid is added and the mixture is stirred at reflux for 4 days. After cooling, the reaction mixture is concentrated to dryness by evaporation and the residue is crystallised from water, yielding stamping compound (a), m.p. >230°: 1H--NMR (DMSO-d6 /D2O): δ=8.16 (d, 1H; 7.9 (d, 1H; 7.55 (t, 1H; 3.28 (m,2H); 2.9 (m,2H); IR(Nujol): 2190 cm-1 (CN).

Workup

  1. temperatureat reflux for 4 days
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated to dryness by evaporation
  4. customthe residue is crystallised from water

Sources & evidence

ORD record
ord-814ec35893454e50a62679f8676a10b0
Source dataset
uspto-grants-1997_06
Patent number
US05639911

Reaction notes

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