4-Bromoaniline → HCID 67316421, compound

HRID 533236Notes

Reaction equation

HRID 533236 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N([O-])=[O:10].[Na+].[C:13]([O-])(=O)[CH3:14].[Na+].[CH2:18]([O:20][C:21]([CH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28])=[O:22])[CH3:19]>Cl.O>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][CH:3]=1)[NH:6][C:25]([C:24]([O:28][CH2:13][CH3:14])=[O:10])=[C:26]2[CH2:27][CH2:23][C:21]([O:20][CH2:18][CH3:19])=[O:22]

Participants

7

Reactant 4

HCID 78074-BromoanilineHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 67316421HCID 67316421, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-bromoaniline (3.44 g) in 5M aqueous HCl (12 mL) at 0° C. was added 2.5M NaNO2 (1.38 g) in water (20 mL). After the addition, 4.5M sodium acetate (9.23 g) in water (25 mL) was added, followed by 2-oxo-cyclopentanecarboxylic acid ethyl ester (3 mL). The mixture was stirred at 0° C. for 15 minutes, warmed to 19° C. over two hours, and extracted with dichloromethane. The extract was dried (MgSO4), filtered and concentrated. The concentrate was dissolved in 10% H2SO4 in ethanol (22 mL) and refluxed overnight, cooled to room temperature, quenched with water (0.4 L), and filtered.

Workup

  1. additionwas added
  2. temperaturewarmed to 19° C. over two hours
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved in 10% H2SO4 in ethanol (22 mL)
  8. temperaturerefluxed overnight
  9. temperaturecooled to room temperature
  10. customquenched with water (0.4 L)
  11. filtrationfiltered

Sources & evidence

ORD record
ord-badf0219465c45218d5f3ab92312e178
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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