Potassium Hydroxide → 4-(5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-benzamide

HRID 422219Notes

Reaction equation

HRID 422219 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[CH:5]=[CH:4][C:3]1=2.[OH-:21].[K+]>C(O)(C)(C)C>[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][C:13]3[CH:14]=[CH:15][C:16]([C:17]([NH2:18])=[O:21])=[CH:19][CH:20]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 597506514-(5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-benzonitrile

Product 1

HCID 597506504-(5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-benzamideYield 91.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Combine 4-(5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-benzonitrile (5.34, 20.3 mmol), t-butyl alcohol (100 ml), and KOH (5.7 g, 101.5 mmol). After the reaction stirs for 72 hours at room temperature, concentrate under reduced pressure and then add ethyl acetate. Wash the organic phase with water, a brine solution, and then dry the organic layer over Na2SO4. Flash chromatograph using 2/1 CH2Cl2/ethyl acetate eluent to afford 5.20 g, 18.5 mmol (91% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 2.1-2.2 (2H, m), 2.6-2.7 (2H, m), 2.9-3.0 (2H, m), 5.6-6.2 (2H, br m); 6.85 (1H, s), 6.9-7.0 (1H, m), 7.05-7.15 (2H, m), 7.8-7.9 (2H, m) 8.05-8.10 (1H, m); MS m/z 284 (M+3).

Workup

  1. concentrationconcentrate under reduced pressure
  2. washWash the organic phase with water
  3. dry with materiala brine solution, and then dry the organic layer over Na2SO4

Sources & evidence

ORD record
ord-b288371a2d094a37bf3282ce2cddcb34
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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