Ethanol → HCID 86745695, compound

HRID 1030527Notes

Reaction equation

HRID 1030527 reaction equation
S(=O)(=O)(O)[OH:2].[C:6]1([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14](=[O:22])[CH:13]2[C:23]#N)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:25]([OH:27])[CH3:26]>>[C:6]1([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14](=[O:22])[CH:13]2[C:23]([O:27][CH2:25][CH3:26])=[O:2])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 53699573HCID 53699573, compound

Product 1

HCID 86745695HCID 86745695, compound

Procedure

80 g of concentrated sulphuric acid were dropped into a suspension of 4-phenyl-1,2,3,4-tetrahydro-2-oxo-3-quinoline carbonitrile (15 g) in ethanol (70 ml) and the whole was heated to reflux for 1 hour. After cooling the reaction mixture was poured onto ice and the aqueous layer was extracted with ethylacetate. After the usual workup 20 g of raw material were obtained. After purification by flash chromatography technique (Silicagel eluted with methylene dichloride/ethylacetate 85:15) 8.3 g of title compound were obtained. M.p. 178°-180° C.

Workup

  1. temperaturethe whole was heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling the reaction mixture
  4. additionwas poured onto ice
  5. extractionthe aqueous layer was extracted with ethylacetate

Sources & evidence

ORD record
ord-e8b5aab2a7514dd2b4a5eb9fbb889e9e
Source dataset
uspto-grants-1992_04
Patent number
US05106851

Reaction notes

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