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

HRID 747967

Reaction equation

HRID 747967 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-orange 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-orange solid precipitates out

Sources & evidence

ORD record
ord-4b2cddca66ef48c48ecd3cbdc4be3ebd
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Linked notes

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