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

HRID 926516Notes

Reaction equation

HRID 926516 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

6

Reactant 4

HCID 78074-BromoanilineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 37964503-(4-Bromoanilino)-3-oxopropanoic acidHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 546894466-Bromo-4-hydroxyquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

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

Sources & evidence

ORD record
ord-9798c8f17dfa47a48113e5e2b0d967ea
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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