Water → 3-Bromobenzene-1,2-diamine

HRID 475133Notes

Reaction equation

HRID 475133 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[Br:12]N1C(=O)CCC1=O.O>CC#N>[Br:12][C:6]1[CH:7]=[CH:2][CH:3]=[C:4]([NH2:9])[C:5]=1[NH2:8]

Participants

5

Reactant 3

HCID 962WaterHCID 69794-Chloro-2-nitroanilineHCID 67184N-bromobutanimide

Product 1

HCID 124898393-Bromobenzene-1,2-diamineYield 119.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-chloro-2-nitrobenzenamine (2.0 g, 11.59 mmol) and 1-bromopyrrolidine-2,5-dione (2.3 g, 12.75 mmol) in MeCN (30 mL) was stirred at 70° C. for 14 h. The reaction mixture was poured into water (100 mL) and stirred at RT for 1 h. The precipitate was filtered and washed with water. The solid was dried under vacuum to afford 3-bromobenzene-1,2-diamine as a yellow solid (2.6 g, 86.7%).

Workup

  1. stirringstirred at RT for 1 h
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-168dde2b1284497fbd2eeb53a3baf81b
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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