4-Bromoaniline → 1-((4-Bromophenyl)diazenyl)pyrrolidine

HRID 522665Notes

Reaction equation

HRID 522665 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N:9]([O-])=O.[Na+].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>Cl.O.[OH-].[K+]>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[N:9][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 78074-BromoanilineHCID 31268PyrrolidineHCID 23668193Sodium Nitrite

Product 1

HCID 3903941-((4-Bromophenyl)diazenyl)pyrrolidineYield 60%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromoaniline (1.7 g, 9.88 mmol) in conc. HCl (2 mL) was added a solution of NaNO2 (682 mg, 9.88 mmol) in water (3 mL) at 0° C. The solution was stirred at 0° C. for 10 minutes, followed by the addition of pyrrolidine (844 mg, 11.86 mmol) in KOH solution (1 mL, 1 N). The resultant mixture was stirred at 0° C. for 0.5 h. The formed precipitate was collected by filtration, washed with 1 mL of ethanol and dried to give the title compound as a yellow solid (1.5 g, yield 60%). MS (ES+) C10H12BrN3 requires: 253, 255, found 254, 256 [M+H]+, purity: 93%.

Workup

  1. filtrationThe formed precipitate was collected by filtration
  2. washwashed with 1 mL of ethanol
  3. customdried

Sources & evidence

ORD record
ord-064cb2035ef646a2bdf793158a04c4c1
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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