Ethanol → HCID 10421737, compound

HRID 275367Notes

Reaction equation

HRID 275367 reaction equation
C1(C)C=CC=CC=1N[N:8]=[C:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH3:10].[CH2:20](O)[CH3:21].OS(O)(=O)=O>O>[CH3:10][C:9]1[NH:8][C:11]2[C:12]([C:11]=1[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)=[CH:13][C:20]([CH3:21])=[CH:10][CH:9]=2

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 86748486HCID 86748486, compound

Product 1

HCID 10421737HCID 10421737, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude hydrazone (100 g), ethanol (700 ml) and conc. aqueous H2SO4 (40 ml) were refluxed for 18 h. After cooling to room temperature water (0.5 l) was added. The thus obtained mixture was extracted with (2×700 ml) ethyl acetate and the combined organic phases were washed with brine, dried and the solvents were evaporated in vacuo. This afforded the title compound, which was purified by column chromatography on silica gel (eluted with ethyl acetate/heptane 1:4) and crystallized from heptane. Yield: 75.5 g, mp:124°-128° C. In a corresponding manner the following indole derivative was prepared: 5-Chloro-3-phenyl-2-methyl-1H-indole 24b, (oil).

Workup

  1. additionwas added
  2. extractionThe thus obtained mixture was extracted with (2×700 ml) ethyl acetate
  3. washthe combined organic phases were washed with brine
  4. customdried
  5. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-2d77a30fc3ed4821b75f7a6ff374639d
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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