O-Phenylenediamine → HCID 11289659, compound

HRID 895502Notes

Reaction equation

HRID 895502 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].Br[CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=1)[C:11](O)=[O:12].[OH-].[Na+]>>[Br:20][C:16]1[CH:15]=[C:14]([CH:10]2[NH:8][C:1]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:7][C:11]2=[O:12])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 7243O-PhenylenediamineHCID 14798Sodium HydroxideHCID 18951130HCID 18951130, compound

Product 1

HCID 11289659HCID 11289659, compound

Conditions

Temperature
60 °C

Procedure

Ortho-phenylenediamine is treated with a suitably substituted bromoacetic acid derivative, such as 2-bromo-2-(3-bromophenyl)acetic acid, in basic medium, such as aqueous sodium hydroxide, which upon warming to 60° C. and then maintaining at this temperature for 30 minutes, affords the product 3-(3-bromophenyl)-1,2,3,4-tetrahydro-2-quinoxalinone as a precipitate.

Workup

  1. temperaturemaintaining at this temperature for 30 minutes

Sources & evidence

ORD record
ord-c5d93a68e4da4d65a06ae9c5c30219ce
Source dataset
uspto-grants-2005_07
Patent number
US06916805B2

Reaction notes

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