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

HRID 2082910Notes

Reaction equation

HRID 2082910 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 (x6). 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-hydrochloride acid (x6). The combined acid extracts were neutralised to pH 7-8 by the addition of sodium bicarbonate. The resulting suspensions was extracted with ether (x4). 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 (x6)
  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-hydrochloride acid (x6)
  12. additionThe combined acid extracts were neutralised to pH 7-8 by the addition of sodium bicarbonate
  13. extractionThe resulting suspensions was extracted with ether (x4)
  14. washThe combined ether extracts were washed twice with water
  15. dry with materialdried (Na2SO4)
  16. customevaporated

Sources & evidence

ORD record
ord-25c980b134fd4bc2b6637b7bb134f323
Source dataset
uspto-grants-1978_04
Patent number
USRE029608

Reaction notes

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