Hydrochloric Acid → HCID 11095700, compound

HRID 1636601Notes

Reaction equation

HRID 1636601 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH2:12][C:13](OCC)=[O:14])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:18])[CH2:5][CH2:6]2.CC(C)([O-])C.[K+].O.Cl>C1(C)C=CC=CC=1>[NH:1]1[C:13](=[O:14])[CH2:12][O:11][C:10]2[CH:9]=[CH:8][C:7]3[CH2:6][CH2:5][C:4](=[O:18])[C:3]=3[C:2]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10911907HCID 10911907, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11095700HCID 11095700, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl [(4-amino-3-oxoindan-5-yl) oxy]acetate (8.7 g, 34.9 mmol.) in toluene (200 mL) was added potassium t-butoxide (400 mg, 3.6 mmol.). The mixture was refluxed for 12 hours under argon atmosphere. The reaction mixture was cooled, which was poured into water, followed by neutralization with dilute hydrochloric acid. The organic matter was extracted with ethyl acetate, which was washed with a saturated aqueous saline solution and water, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography (hexane:ethyl acetate=1:1) to afford the title compound (yield 4.8 g, 66%).

Workup

  1. temperatureThe mixture was refluxed for 12 hours under argon atmosphere
  2. temperatureThe reaction mixture was cooled
  3. extractionThe organic matter was extracted with ethyl acetate, which
  4. washwas washed with a saturated aqueous saline solution and water
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by means of silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-24875961a36f4bb18170512f8412fa32
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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