Hydrochloric Acid → 5-Amino-2-fluorobenzonitrile

HRID 1706640Notes

Reaction equation

HRID 1706640 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>C(O)C>[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 2

HCID 313Hydrochloric AcidHCID 5540822,4-Dinitrobenzonitrile

Product 1

HCID 132271905-Amino-2-fluorobenzonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 74.6 g. of stannous chloride dihydrate, 75 ml. concentrated HCl, and 150 ml. ethanol was cooled in an ice bath and stirred while adding 9.66 g. (0.05 mole) of powdered 2,4-dinitrobenzonitrile at a rate that maintained a temperature of 25°-30° C. The resulting yellow solution was held at 40° C. for 90 minutes while a stream of nitrogen was blown over the surface to evaporate most ot the ethanol. The residue was a yellow slurry, which was cooled in an ice bath and stirred while a solution of 70 g. NaOH in 280 g. of water was added slowly. The mixture was then filtered. The filtrate was extracted four times with ethyl acetate and the extract evaporated to dryness. The residue was combined with the solids from the filtration, and the mixture was extracted with four 150 ml. portions of boiling benzene. The benzene solution was evaporated to dryness to give 4.75 g. of crude product, which was recrystallized from benzene to give 4.67 g. (70% yield) of pure 2,4-diaminobenzonitrile, m.p. 105° C. Anal. Calculated for C7H7N3 : C, 63.19; H, 5.30; N, 31.56. Found: C, 62.54, 62.67; H, 5.24, 5.09; N, 31.32, 31.10.

Workup

  1. additionwhile adding 9.66 g
  2. customto evaporate most ot the ethanol
  3. temperaturewas cooled in an ice bath
  4. stirringstirred while a solution of 70 g
  5. additionof water was added slowly
  6. filtrationThe mixture was then filtered
  7. extractionThe filtrate was extracted four times with ethyl acetate
  8. customthe extract evaporated to dryness
  9. filtrationThe residue was combined with the solids from the filtration
  10. extractionthe mixture was extracted with four 150 ml
  11. customThe benzene solution was evaporated to dryness
  12. customto give 4.75 g
  13. customof crude product, which was recrystallized from benzene
  14. customto give 4.67 g

Sources & evidence

ORD record
ord-e9c9a7e28c6d43c18cd8baad7ac8e12e
Source dataset
uspto-grants-1980_06
Patent number
US04208343

Reaction notes

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