Sodium Hydroxide → 6-Bromo-3-phenylquinolin-4(1H)-one

HRID 627469Notes

Reaction equation

HRID 627469 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[CH:9][CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([O:13]CC)=O)=[CH:4][CH:3]=1.[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][CH:9]=[C:10]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:11]2=[O:13]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86716060Ethyl 3-((4-bromophenyl)imino)-2-phenylpropanoate

Product 1

HCID 867160616-Bromo-3-phenylquinolin-4(1H)-one

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 3-((4-bromophenyl)imino)-2-phenylpropanoate (6.18 g, 17.8 mmol, Intermediate 3, step a) and polyphosphoric acid (8.90 g) was heated at 150° C. for 1.5 hours. After cooling to room temperature, 3 N NaOH was added at 4° C. until basic. The solid was filtered, washed with water, and dried under vacuum overnight to give the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-55c3b0d1fb3e41f3afbace124e9ea4ad
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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