Hydrochloric Acid → Dimethyl-2,5-bis[(4-bromophenyl)amino]cyclohexa-1,4-diene-1,4-dicarboxylate

HRID 2056965Notes

Reaction equation

HRID 2056965 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:11](=O)[CH2:10][CH:9]([C:13]([O:15][CH3:16])=[O:14])[C:7](=O)[CH2:6]1)=[O:4].[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.Cl>CO>[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:7]2[CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:11]([NH:22][C:21]3[CH:23]=[CH:24][C:18]([Br:17])=[CH:19][CH:20]=3)[CH2:10][C:9]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 78074-BromoanilineHCID 948661,4-Cyclohexanedicarboxylic acid, 2,5-dioxo-, 1,4-dimethyl ester

Product 1

HCID 57587328Dimethyl-2,5-bis[(4-bromophenyl)amino]cyclohexa-1,4-diene-1,4-dicarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate (4.56 gm; 20 mmol) and methanol (100 ml) were heated to boiling, then 4-bromoaniline (6.88 gm; 40 mmol) was added followed by conc. hydrochloric acid (200 μl). The mixture was refluxed for 5 hours under a nitrogen atmosphere. On cooling a cream solid precipitated out which was collected by filtration, washed with methanol and dried under vacuum to give 10.18 gm (95%) of dimethyl 2,5-bis{(4-bromophenyl)amino}cyclohexa-1,4-diene-1,4-dicaboxylate.

Workup

  1. temperatureThe mixture was refluxed for 5 hours under a nitrogen atmosphere
  2. temperatureOn cooling a cream solid
  3. customprecipitated out which
  4. filtrationwas collected by filtration
  5. washwashed with methanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-26672ec426fd436fa9e16a441925733c
Source dataset
uspto-grants-2008_02
Patent number
US07335771B2

Reaction notes

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