Ethanol → Ethyl 4-amino-5-cyano-2-hydroxybenzoate

HRID 249935Notes

Reaction equation

HRID 249935 reaction equation
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].[Na].C(O[CH:11]=[C:12]([C:15]#[N:16])[C:13]#[N:14])C.[CH2:17]([OH:19])[CH3:18]>>[CH2:5]([O:4][C:1](=[O:3])[C:2]1[CH:11]=[C:12]([C:13]#[N:14])[C:15]([NH2:16])=[CH:18][C:17]=1[OH:19])[CH3:6]

Participants

5

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 671522-(Ethoxymethylene)propanedinitrileHCID 5360545Sodium

Product 1

HCID 3018374Ethyl 4-amino-5-cyano-2-hydroxybenzoateYield 29%

Procedure

According to H.-W-. Schmidt et al. (Liebigs Ann. Chem. 1979, 2005-10), ethyl acetate (42 g, 323 mmol) is added to a solution of sodium (15 g, 23 mmol) in ethanol (4.0 l) and the mixture is stirred at room temperature for 30 minutes. Ethoxymethylene-malononitrile (40.6 g, 332 mmol) is added. After 30 minutes at 80° C., the reaction mixture is allowed to cool to room temperature and the resulting precipitate is filtered off with suction. The precipitate is dissolved using water, and the aqueous phase is acidified with concentrated hydrochloric acid and the resulting precipitate is filtered off with suction again. After recrystallization from acetic acid, the crystals are filtered off with suction, washed with water and subsequently dried. The desired product is obtained in 29% yield (21.5 g).

Workup

  1. waitAfter 30 minutes at 80° C.
  2. temperatureto cool to room temperature
  3. filtrationthe resulting precipitate is filtered off with suction
  4. dissolutionThe precipitate is dissolved
  5. filtrationthe resulting precipitate is filtered off with suction again
  6. customAfter recrystallization from acetic acid
  7. filtrationthe crystals are filtered off with suction
  8. washwashed with water
  9. customsubsequently dried

Sources & evidence

ORD record
ord-df35b0d162734dd5875ff5f1535288ca
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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