Ethanol → 3′,4′-Dihydro-6′-methoxyspiro[imidazolidine-4,1′(2′H)-naphthalene]-2,5-dione

HRID 1757147Notes

Reaction equation

HRID 1757147 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2.[C-]#N.[K+].[C:17](=[O:20])([O-])[O-].[NH4+:21].[NH4+:22].C[CH2:24][OH:25]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]1([C:24](=[O:25])[NH:22][C:17](=[O:20])[NH:21]1)[CH2:8][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 141126-Methoxy-alpha-tetraloneHCID 517111Ammonium Carbonate

Product 1

HCID 29981393′,4′-Dihydro-6′-methoxyspiro[imidazolidine-4,1′(2′H)-naphthalene]-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 35.2 g (0.2 mol) of 6-methoxy-1-tetralone, 19.5 g (0.3 mol) of potassium cyanide and 134.4 g (1.4 mol) of ammonium carbonate in 280 mL of EtOH was placed in a stainless steel bomb and heated at 110° C. for 48 hours. After cooling, the mixture was poured in 1.4 L of water. It was allowed to sit at ambient temperature for 3 days. The precipitated solid was filtered and washed several times with water and dried to give 48.1 g of a brown solid: mp 218°-220° C. 1H-NMR (DMSO-d6)d10.75(s, 1H),8.45(s, 1H),6.96(d, 1H),6.79 (d, 1H), 6.70 (s, 1H), 3.72 (s, 3H), 2.73 (t, 2H), 1.70-2.20 (m, 4H).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitated solid was filtered
  3. washwashed several times with water
  4. customdried

Sources & evidence

ORD record
ord-e9803c80fb424abdb5adb117e7dd26f2
Source dataset
uspto-grants-1995_08
Patent number
US05444079

Reaction notes

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