Potassium Hydroxide → 4-(1-Oxo-indan-5-yloxy)-benzamide

HRID 422217

Reaction equation

HRID 422217 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[OH-:20].[K+]>C(O)(C)(C)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:19]=[CH:18][C:15]([C:16]([NH2:17])=[O:20])=[CH:14][CH:13]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 597506434-(1-Oxo-indan-5-yloxy)-benzonitrile

Product 1

HCID 597506634-(1-Oxo-indan-5-yloxy)-benzamideYield 5.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Combine 4-(1-Oxo-indan-5-yloxy)-benzonitrile (1.64 g, 6.58 mmol), tert-butyl alcohol (50 ml), and grounded KOH (1.85 g, 32.89 mmol) at room temperature under nitrogen atmosphere. Stir the reaction for 24 hours then concentrate under reduced pressure. Add Ethyl acetate to the reaction mixture and wash with brine. Dry the organic layer over Na2SO4. A yellow-mange solid precipitates out to afford 101.0 mg, 0.38 mmol (5.7% yield) of the title compound: No Characterization—Characterized by sequential reaction.

Workup

  1. customat room temperature
  2. customthe reaction for 24 hours
  3. concentrationthen concentrate under reduced pressure
  4. washAdd Ethyl acetate to the reaction mixture and wash with brine
  5. dry with materialDry the organic layer over Na2SO4
  6. customA yellow-mange solid precipitates out

Sources & evidence

ORD record
ord-6f3198d2da994130a586221560d03f30
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Linked notes

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