Water → HCID 90403883, compound

HRID 1468963Notes

Reaction equation

HRID 1468963 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-])=[O:10])[C:3]=1[Cl:12].[OH-:13].[K+].O>C(O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]2=[N+:6]([O-:13])[O:10][N:9]=[C:4]2[C:3]=1[Cl:12]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 265991564-Bromo-3-chloro-2-nitroaniline

Product 1

HCID 90403883HCID 90403883, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-2.5 °C

Procedure

4-Bromo-3-chloro-2-nitroaniline (4.1 g, 16 mmol) was dissolved in 60 mL ethanol, treated with 45% potassium hydroxide solution (2.0 g, 16 mmol), cooled to −5 to 0° C. and treated drop wise with commercial bleach solution (32 mL, 6 wt. %, 31 mmol) over 20 min. The mixture was stirred for 90 min at 0-15° C. and poured into 700 mL water. The precipitated product was collected by filtration, washed well with water and then dried under vacuum at 80° C. to give the title compound (3.2 g, 81%): EIMS m/z 248.

Workup

  1. additiontreated drop wise with commercial bleach solution (32 mL, 6 wt. %, 31 mmol) over 20 min
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed well with water
  4. customdried under vacuum at 80° C.

Sources & evidence

ORD record
ord-77b9f7b6865c4255ad259a98d8f60656
Source dataset
uspto-grants-2015_04
Patent number
US09006250B2

Reaction notes

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