Hydrochloric Acid → 6-Bromo-3-(3-chlorophenyl)-4-hydroxyquinolin-2(1H)-one

HRID 627541Notes

Reaction equation

[Li]CCCC.C[Si](C)(C)N[Si](C)(C)C.[Br:15][C:16]1[CH:17]=[CH:18][C:19]([NH:26][C:27](=[O:36])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)=[C:20]([CH:25]=1)[C:21]([O:23]C)=O.Cl>C1COCC1>[Br:15][C:16]1[CH:25]=[C:20]2[C:19](=[CH:18][CH:17]=1)[NH:26][C:27](=[O:36])[C:28]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)=[C:21]2[OH:23]

Participants

Conditions

Temperature: -40 °C

Procedure

n-BuLi (1.6 M in hexane, 79 mL, 126 mmol) was added dropwise to a mixture of hexamethyldisilazane (26.7 mL, 126 mmol) in THF (150 mL) at −78° C. under nitrogen. The mixture was stirred for 1 hour, then was warmed to −40° C. A solution of methyl 5-bromo-2-(2-(3-chlorophenyl)acetamido)benzoate (21.1 g, 55 mmol, Intermediate 60, step a) in THF (150 mL) was added. The mixture was allowed to warm to room temperature and ice was added. The aqueous phase was acidified with 6 N aqueous HCl. The precipitate was collected by filtration, washed with DCM, and air-dried to yield the title compound.

Workup

temperatureto warm to room temperature
additionice was added
filtrationThe precipitate was collected by filtration
washwashed with DCM
customair-dried

Sources & evidence

ORD record: ord-e1d7c9a46ee6426ca096bf869f061746
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309222B2

Reaction notes

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