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

HRID 1095765Notes

Reaction equation

HRID 1095765 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+]>O1CCCC1>[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 tetrahydrofuran (THF) (60 mL) was added via syringe pump (1 mL/min) to a solution of potassium bis(trimethylsilyl)amide (KHMDS) (150 mL, 0.5M PhMe, 75 mmol) at −78° C. under N2. The reaction was allowed to slowly warm to room temperature 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. customthe layers were separated
  2. washThe aqueous was washed with ether (150 mL)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-5b64661c08574b719b267aa7f07b129a
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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