4-Bromoaniline → HCID 22647397, compound

HRID 393758Notes

Reaction equation

HRID 393758 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]([CH3:16])[C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9](Cl)[CH:8]=2)=[C:4]([CH3:17])[CH:3]=1.[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:15]=[C:14]([CH3:16])[C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:23][C:22]3[CH:24]=[CH:25][C:19]([Br:18])=[CH:20][CH:21]=3)[CH:8]=2)=[C:4]([CH3:17])[CH:3]=1

Participants

5

Reactant 2

HCID 78074-BromoanilineHCID 22647396HCID 22647396, compound

Product 1

HCID 22647397HCID 22647397, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flask outfitted with a reflux condensor, 15 (1 g, 3.2 mmol) and 4-bromoaniline (1.1 g, 6.4 mmol, 2 equiv) were melted together at 190° C. for 5 h. The reaction was cooled to room temperature and the resulting black solid was dissolved in 4:1 THF-1N NaOH soln (5 mL) stirring overnight. The reaction was diluted with EtOAc and the organic phase was washed with 1 N NaOH soln, 0.1 M HCl soln. Activated charcoal was added and the organic phase was stirred at room temperature for 0.5 h, filtered through celite and concentrated. The resulting brown solid was recrystallized from CH2Cl2 (˜4 mL) to provide the purified product as a white solid (1.2 g, 86%). 1H NMR (300 MHz, CDCl3) δ8.03 (d, J=5.9 Hz, 1H), 7.39 (d, J=8.8 Hz, 2H), 7.23 (m, 3H), 6.42 (s, NH), 6.19 (m, 2H), 6.14 (d, J=1.9 Hz, 1H), 2.10 (s, 6H).

Workup

  1. washthe organic phase was washed with 1 N NaOH soln
  2. additionActivated charcoal was added
  3. stirringthe organic phase was stirred at room temperature for 0.5 h
  4. filtrationfiltered through celite and
  5. concentrationconcentrated
  6. customThe resulting brown solid was recrystallized from CH2Cl2 (˜4 mL)

Sources & evidence

ORD record
ord-4aa46ece6d9f4d958b6331e19c864190
Source dataset
uspto-grants-2004_10
Patent number
US06809109B2

Reaction notes

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