N,N-Diethylaniline → HCID 20185126, compound

HRID 2309387Notes

Reaction equation

HRID 2309387 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12]CC=C)=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:16])[CH3:2].C(N(CC)[C:20]1[CH:25]=CC=C[CH:21]=1)C>>[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([CH2:25][CH:20]=[CH2:21])[C:8]([OH:12])=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:16])[CH3:2]

Participants

3

Reactant 2

HCID 7061N,N-DiethylanilineHCID 20185155HCID 20185155, compound

Product 1

HCID 20185126HCID 20185126, compoundYield 12%

Procedure

A solution of 1.09 g. (5.02 mmoles) of 1-ethyl-5-allyloxyoxindole in 5 ml. of N,N-diethylaniline was heated at reflux for 1 hour. The cooled reaction was added to ice cold 1N hydrochloric acid and the mixture extracted with methylene chloride. The extract was washed with water (3×), saturated brine solution (1×) and dried over magnesium sulfate. The residue remaining after the solvent was removed was chromatographed on 22 g. of silica gel using 50-100% diethyl ether-hexane as the eluent to give 134 mg. (12% yield) of 1-ethyl-4-allyl-5-hydroxyoxindole and 644 mg. (59% yield) of 1-ethyl-5-hydroxy-6-allyloxindole, m.p. 130°-131° C.

Workup

  1. temperatureat reflux for 1 hour
  2. customThe cooled reaction
  3. extractionthe mixture extracted with methylene chloride
  4. washThe extract was washed with water (3×), saturated brine solution (1×)
  5. dry with materialdried over magnesium sulfate
  6. customwas removed
  7. customwas chromatographed on 22 g
  8. customof silica gel using 50-100% diethyl ether-hexane as the eluent to give 134 mg

Sources & evidence

ORD record
ord-29c5dae78599467cab1bd0146c5eac2b
Source dataset
uspto-grants-1987_09
Patent number
US04695571

Reaction notes

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