Water → 6-Bromo-4-hydroxy-3-phenoxyquinolin-2(1H)-one

HRID 520840Notes

Reaction equation

HRID 520840 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:22])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].C[Si]([N-][Si](C)(C)C)(C)C.[K+].O>O1CCCC1>[Br:1][C:2]1[CH:11]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:12][C:13](=[O:22])[C:14]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:7]2[OH:8]

Participants

5

Reactant 3

HCID 962WaterHCID 3251421Potassium bis(trimethylsilyl)amideHCID 7765744Methyl 5-bromo-2-(2-phenoxyacetamido)benzoate

Product 1

HCID 867154446-Bromo-4-hydroxy-3-phenoxyquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 5-bromo-2-(2-phenoxyacetamido)benzoate (7.28 g, 20.0 mmol, Intermediate 5: step a) in tetrahydrofuran (215 mL) at −78° C. was added potassium bis(trimethylsilyl)amide (0.5 M solution in toluene, 118.7 mL, 59.37 mmol) over 7 minutes. The mixture was stirred at −78° C. for 5 minutes and 0° C. for 1.5 hours. The resulting cold solution was quenched with water. The white solid formed was completely dissolved by addition of excess water. The aqueous phase was washed once with EtOAc and then acidified by slow addition of 2 N aqueous HCl solution (kept pH above 2). The off-white precipitate formed was filtered and dried in the air overnight and at 40° C. for 1 hour to provide the title compound.

Workup

  1. customThe resulting cold solution was quenched with water
  2. customThe white solid formed
  3. washThe aqueous phase was washed once with EtOAc
  4. additionacidified by slow addition of 2 N aqueous HCl solution (kept pH above 2)
  5. customThe off-white precipitate formed
  6. filtrationwas filtered
  7. customdried in the air overnight and at 40° C. for 1 hour

Sources & evidence

ORD record
ord-c8032877c4bc4c1995aa4c6690107a70
Source dataset
uspto-grants-2016_05
Patent number
US09328095B2

Reaction notes

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