Ethylene Glycol → HCID 21476735, compound

HRID 2293440Notes

Reaction equation

HRID 2293440 reaction equation
C([N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18](=O)[CH2:19][CH2:20][CH:11]([C:12]=23)[CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[K+].O.NN.C(O)CO>O>[NH:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[CH2:18][CH2:19][CH2:20][CH:11]([C:12]=23)[CH2:10]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 570263HCID 570263, compound

Product 1

HCID 21476735HCID 21476735, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5.0 g of 1-benzoyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one, 2.7 g of potassium hydroxide, 2 ml of hydrazine hydrate and 20 ml of ethylene glycol was heated at 120° C. for 2 hours and then at 190° C. for 3 hours. After mixture cooling, water was added, and the reaction product was extracted with dichloromethane. After the extract was dried over magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: dichloromethane-ethyl acetate=10:1 (v/v)) to yield 1.9 g of 1,2,2a,3,4,5-hexahydrobenz[cd]indole as a colorless crystal having a melting point of 58° to 59° C.

Workup

  1. temperatureAfter mixture cooling
  2. extractionthe reaction product was extracted with dichloromethane
  3. dry with materialAfter the extract was dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (developing solvent: dichloromethane-ethyl acetate=10:1 (v/v))

Sources & evidence

ORD record
ord-313c0d0374104e339d03feb516a1b96f
Source dataset
uspto-grants-1997_11
Patent number
US05686466

Reaction notes

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