4-Bromoaniline → 6-Bromo-4-hydroxyquinolin-2(1H)-one

HRID 1507300Notes

Reaction equation

BrC1C=CC(N)=CC=1.CC1(C)OC(=O)CC(=O)O1.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:32])[CH2:28][C:29]([OH:31])=O)=[CH:22][CH:21]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[Br:19][C:20]1[CH:21]=[C:22]2[C:23](=[CH:24][CH:25]=1)[NH:26][C:27](=[O:32])[CH:28]=[C:29]2[OH:31]

Participants

Conditions

Temperature: 80 °C

Procedure

According to the general method described in Synthetic Communications 2010, 40, 732, a mixture of 4-bromoaniline (30.0 g, 174 mmol) and 2,2-dimethyl-1,3-dioxan-4,6-dione (25.1 g, 174 mmol) was heated to 80° C. for 1.5 hours and cooled to ambient temperature to receive 3-((4-bromophenyl)amino)-3-oxopropanoic acid. The acetone byproduct was removed under vacuum to provide the intermediate product as a dry solid. Eaton's reagent (100 mL) was added to the solid and the resulting mixture heated to 70° C. overnight then cooled to room temperature. The mixture was poured into water and the brown precipitate was filtered and rinsed with water. The brown precipitate was triturated with ethanol, then filtered to provide the title compound as a light brown solid.

Workup

temperaturecooled to ambient temperature
customThe acetone byproduct was removed under vacuum
customto provide the intermediate product as a dry solid
temperaturethe resulting mixture heated to 70° C. overnight
temperaturethen cooled to room temperature
filtrationthe brown precipitate was filtered
washrinsed with water
customThe brown precipitate was triturated with ethanol
filtrationfiltered

Sources & evidence

ORD record: ord-a9772e451f44434cb8eacf362b49044c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221804B2

Reaction notes

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