4-Amino-3-chlorobenzonitrile → 3-Chloro-4-nitrobenzonitrile

HRID 433018

Reaction equation

HRID 433018 reaction equation
[N:1]([O-:3])=[O:2].[Na+].N[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[Cl:14]>O.Cl>[Cl:14][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:6]=1[N+:1]([O-:3])=[O:2])[C:10]#[N:11]

Participants

5

Reactant 2

HCID 5198964-Amino-3-chlorobenzonitrileHCID 23668193Sodium Nitrite2×

Product 1

HCID 149730283-Chloro-4-nitrobenzonitrileYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium nitrite (6.78 g in water (40 mL) at 0° C.) was slowly added to a solution of 4-amino-3-chloro-benzonitrile (10.5 g) in water (30 mL) and concentrated hydrochloric acid (30 mL) also at 0° C. After 10 minutes the solution was poured onto a suspension of cuprous oxide (3.48 g) and sodium nitrite (31.69 g) in water (100 mL) at 0° C. The ensuing mixture was stirred at 0° C. for 1 hour then at 23° C. for 1 hour. The resulting mixture was extracted with dichloromethane and the organic layer washed with saturated sodium chloride. The separated organic layer was dried over sodium sulfate and then concentrated to give 3-chloro-4-nitro-benzonitrile (11.31 g).

Workup

  1. waitat 23° C. for 1 hour
  2. extractionThe resulting mixture was extracted with dichloromethane
  3. washthe organic layer washed with saturated sodium chloride
  4. dry with materialThe separated organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-69e7e0f0929e4c93a5729018f30478f0
Source dataset
uspto-grants-2003_12
Patent number
US06664395B2

Linked notes

Loading…