Potassium bis(trimethylsilyl)amide → 8-(cyclopentyloxy)-4-hydroxy-7-methoxyquinolin-2(1H)-one

HRID 1522805Notes

Reaction equation

HRID 1522805 reaction equation
[C:1]([NH:4][C:5]1[C:14]([O:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:13]([O:21][CH3:22])[CH:12]=[CH:11][C:6]=1[C:7](OC)=[O:8])(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[CH:16]1([O:15][C:14]2[C:13]([O:21][CH3:22])=[CH:12][CH:11]=[C:6]3[C:5]=2[NH:4][C:1](=[O:3])[CH:2]=[C:7]3[OH:8])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 66781936Methyl 2-acetamido-3-(cyclopentyloxy)-4-methoxybenzoate

Product 1

HCID 667818648-(cyclopentyloxy)-4-hydroxy-7-methoxyquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-acetamido-3-(cyclopentyloxy)-4-methoxybenzoate (6.42 g, 20.9 mmol) and anhydrous THF (60 mL) was added via syringe pump (1 mL/min) to a solution of KHMDS (150 mL, 0.5M PhMe, 75 mmol) at −78° C. under N2. The reaction was allowed to slowly warm to rt as the bath expired overnight. After 17 h, the reaction was poured into ice/water (250 mL), let stir for 10 min, and the layers were separated. The aqueous was washed with ether (150 mL), acidified with conc. HCl (7 mL), and filtered to give 8-(cyclopentyloxy)-4-hydroxy-7-methoxyquinolin-2(1H)-one: MS (ESI): 276.0.

Workup

  1. waitAfter 17 h
  2. customthe layers were separated
  3. washThe aqueous was washed with ether (150 mL)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c2bfa3daf5604e61943ee047578b6bb5
Source dataset
uspto-grants-2015_07
Patent number
US09078887B2

Reaction notes

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