Ethanol → HCID 13592496, compound

HRID 1761412Notes

Reaction equation

HRID 1761412 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[CH:12]([CH3:14])[CH3:13].C(O)C.[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl.[OH-].[K+]>O>[O:22]1[CH2:21][CH:20]1[CH2:18][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[CH:12]([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 13592494HCID 13592494, compound

Product 1

HCID 13592496HCID 13592496, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18 g. 5-Hydroxy-3-isopropylindolinone are dissolved in 150 ml. ethanol, 22 ml. epichlorohydrin are added thereto, the mixture is mixed with 5.3 g. potassium hydroxide in 5 ml. water and the reaction mixture is stirred for 2 days at ambient temperature. After the addition of 200 ml. water, the reaction mixture is extracted with ethyl acetate and the extract purified over a column of silica gel with methylene chloride/methanol (95:5 v/v). There are obtained 11 g. of the title compound; yield 50% of theory; m.p. 122°-125° C., after recrystallisation from diethyl ether.

Workup

  1. additionthe mixture is mixed with 5.3 g
  2. additionAfter the addition of 200 ml
  3. extractionwater, the reaction mixture is extracted with ethyl acetate
  4. customthe extract purified over a column of silica gel with methylene chloride/methanol (95:5 v/v)
  5. customThere are obtained 11 g

Sources & evidence

ORD record
ord-12dc917d0e6c479db7934134e73f188f
Source dataset
uspto-grants-1989_05
Patent number
US04826847

Reaction notes

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