Hydrochloric Acid → 2-(3-Amino-4-hydroxyphenyl)propanenitrile

HRID 2397231Notes

Reaction equation

HRID 2397231 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]([CH3:14])[C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[OH:10])([O-])=O.Cl.[OH-].[Na+]>C(O)C.O.C(Cl)(Cl)Cl>[NH2:1][C:4]1[CH:5]=[C:6]([CH:11]([CH3:14])[C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 122026352-(4-Hydroxy-3-nitrophenyl)propanenitrile

Product 1

HCID 122026362-(3-Amino-4-hydroxyphenyl)propanenitrile

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

2-(3-Nitro-4-hydroxyphenyl) propionitrile (123.8 g., 0.64 mole.) was suspended in absolute ethanol (950 ml.) and added during 20 minutes, with cooling, to a solution of stannous chloride dihydrate (437.8 g., 1.94 mole.) in concentrated hydrochloric acid (591 ml., 7 mole.). The addition was made at such a rate that the temperature of the reaction mixture did not exceed 20° C. Stirring of the mixture was continued for a further 19 hours at room temperature. The resulting solution, together with ice (1.75 kg.) was added during one hour to a cooled solution of sodium hydroxide (650 g.) in water (600 ml.). The temperature of the reaction mixture was maintained at 15°-20° C. during the addition. The mixture was stirred for a further 1 hour, and the pH then adjusted to 6 by the addition of concentrated hydrochloric acid. The resulting suspension was filtered and the filtrate saturated with sodium chloride, then extracted with ether (×6). The combined ether extracts were dried (Na2SO4) and evaporated to leave a solid (69.15 g.) which was suspended in chloroform and extracted with 2N-hydrochloric acid (×6). The combined acid extracts were neutralised to pH 7-8 by the addition of sodium bicarbonate. The resulting suspension was extracted with ether (×4). The combined ether extracts were washed twice with water, dried (Na2SO4), and evaporated to yield 2-(3-amino-4-hydroxyphenyl) propionitrile as a light brown solid (62.85 g.), m.p. 110°-112° C.

Workup

  1. additionadded during 20 minutes
  2. additionThe addition
  3. customdid not exceed 20° C
  4. temperatureThe temperature of the reaction mixture was maintained at 15°-20° C. during the addition
  5. stirringThe mixture was stirred for a further 1 hour
  6. filtrationThe resulting suspension was filtered
  7. extractionthe filtrate saturated with sodium chloride, then extracted with ether (×6)
  8. dry with materialThe combined ether extracts were dried (Na2SO4)
  9. customevaporated
  10. customto leave a solid (69.15 g.) which
  11. extractionextracted with 2N-hydrochloric acid (×6)
  12. additionThe combined acid extracts were neutralised to pH 7-8 by the addition of sodium bicarbonate
  13. extractionThe resulting suspension was extracted with ether (×4)
  14. washThe combined ether extracts were washed twice with water
  15. dry with materialdried (Na2SO4)
  16. customevaporated

Sources & evidence

ORD record
ord-a164f7ba6e8747488ae7b7718c46102d
Source dataset
uspto-grants-1977_05
Patent number
US04021440

Reaction notes

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