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

HRID 520846Notes

Reaction equation

HRID 520846 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 Synth. Commun. 2010, 40, 732, a mixture of 4-bromoaniline (10.0 g, 58.1 mmol) and 2,2-dimethyl-1,3-dioxan-4,6-dione (8.40 g, 58.1 mmol) was heated at 80° C. for 1 hour and cooled to room temperature to receive 3-((4-bromophenyl)amino)-3-oxopropanoic acid as a solid. A stream of nitrogen gas was passed over the solid product to remove liquid acetone formed as a by-product. To this solid was added Eaton's reagent (40 mL) and the mixture was heated at 70° C. for 12 hours and then cooled to room temperature. To the resulting mixture was added water and stirred vigorously to receive a suspension which was filtered. The solid residue was washed with water and dried in air to yield the title compound.

Workup

  1. temperaturecooled to room temperature
  2. customto remove liquid acetone
  3. customformed as a by-product
  4. temperaturethe mixture was heated at 70° C. for 12 hours
  5. temperaturecooled to room temperature
  6. filtrationwas filtered
  7. washThe solid residue was washed with water
  8. customdried in air

Sources & evidence

ORD record
ord-dd2d501a788d419c98884c7011fe3a6c
Source dataset
uspto-grants-2016_05
Patent number
US09328095B2

Reaction notes

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