4-Bromoaniline → HCID 178419396, compound

HRID 44426Notes

Reaction equation

HRID 44426 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 178419396HCID 178419396, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-bromo aniline (133, 10 g, 58.1 mmol) in concentrated HCl (11.7 mL) was added dropwise a solution of NaNO2 (4 g, 57.9 mmol) in H2O (5 mL). The reaction was then stirred for an additional 10 min. at 0° C. after the addition. The resulting diazonium salt solution was added at once to a solution of pyrrolidine (4.54 g, 63.9 mmol) in 1M KOH (50 mL). The reaction mixture was stirred for 30 min at 0-10° C. The resulting precipitate was then filtered and recrystallized from absolute ethanol (50 mL) to give compound 134 (6.8 g, 46.2%) as light yellow crystals.

Workup

  1. additionafter the addition
  2. stirringThe reaction mixture was stirred for 30 min at 0-10° C
  3. filtrationThe resulting precipitate was then filtered
  4. customrecrystallized from absolute ethanol (50 mL)

Sources & evidence

ORD record
ord-c8cdc966383a43d29e2e39b24362a334
Source dataset
uspto-grants-2013_09
Patent number
US08541423B2

Reaction notes

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