Benzaldehyde → HCID 14146582, compound

HRID 1449110Notes

Reaction equation

HRID 1449110 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:15]([C:18]#[N:19])[C:16]#[N:17].[NH:20]1CCO[CH2:22][CH2:21]1>CO>[NH2:17][C:16]1[C:22]([C:21]#[N:20])=[C:5]2[C:1]([CH2:2][CH2:3][CH2:4]2)=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:15]=1[C:18]#[N:19]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8010MalononitrileHCID 8083MorpholineHCID 8452Cyclopentanone

Product 1

HCID 14146582HCID 14146582, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 mol (84 g) of cyclopentanone, 1 mol (106 g) of benzaldehyde and 2 mols (132 g) of malonic acid dinitrile are dissolved in 1 1 of methanol and 60 ml of morpholine are added dropwise over a period of approx. 2 hours in such a way that the temperature of the reaction mixture does not exceed 45° C. The mixture is then stirred for a further 8 hours and the precipitate which forms during the reaction is filtered off. The filter residue is heated in 2 1 of ethanolic KOH for 10 minutes under reflux, the reaction mixture is poured out onto ice/water, the pH is adjusted to 2 with dilute sulphuric acid and the product is filtered off. 155 g of 6-amino-5,7-dicyano-4-phenyl-indane (60% of theory) are obtained, melting point 148°-149° C. (from benzene).

Workup

  1. additionare added dropwise over a period of approx. 2 hours in such a way that the temperature of the reaction mixture
  2. customdoes not exceed 45° C
  3. filtrationis filtered off
  4. temperatureThe filter residue is heated in 2 1 of ethanolic KOH for 10 minutes
  5. temperatureunder reflux
  6. additionthe reaction mixture is poured out onto ice/water
  7. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-5d8313bf9c3047d6b9164c59adde75c5
Source dataset
uspto-grants-1980_02
Patent number
US04189427

Reaction notes

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