Hydrochloric Acid → 5-Amino-2-fluorobenzonitrile

HRID 1834038Notes

Reaction equation

HRID 1834038 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])([O-])=O.[OH-].[Na+]>>[NH2:2][C:5]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5540822,4-Dinitrobenzonitrile

Product 1

HCID 132271905-Amino-2-fluorobenzonitrileYield 80%

Procedure

To a stirred solution of 45.12 grams (0.2 moles) of stannous chloride dihydrate in 100 ml. of concentrated HCl is added, gradually, 5.44 grams (0.0282 moles) of 2,4-dinitrobenzonitrile. An exothermic reaction takes place with the temperature rising to about 80°. The solution is stirred and allowed to come to room temperature over the course of 2 hours. The mixture is made strongly basic by the addition of a 50% sodium hydroxide solution, with cooling, and extracted with methylene chloride. The CH2Cl2 extracts are dried over anhydrous MgSO4 and the solvent removed. There is obtained 3.0 grams (80%) of a yellow solid melting at 102°-3°. Infrared (mull): 3500, 3350, (NH), 2200 (CN) cm-1.

Workup

  1. customAn exothermic reaction
  2. customrising to about 80°
  3. customto come to room temperature over the course of 2 hours
  4. temperaturewith cooling
  5. extractionextracted with methylene chloride
  6. dry with materialThe CH2Cl2 extracts are dried over anhydrous MgSO4
  7. customthe solvent removed

Sources & evidence

ORD record
ord-f9e75f719b69483786fb057515846cc6
Source dataset
uspto-grants-1978_01
Patent number
US04067995

Reaction notes

Loading…