Ethanolamine → 5-Cyano-(2-hydroxyethyl)salicylamide

HRID 374440Notes

Reaction equation

HRID 374440 reaction equation
CO[C:3](=[O:13])[C:4]1[C:5](=[CH:7][CH:8]=[C:9]([C:11]#[N:12])[CH:10]=1)[OH:6].[CH2:14]([CH2:16]N)[OH:15].C(#[N:20])C>>[C:11]([C:9]1[CH:10]=[C:4]([C:3]([NH2:20])=[O:13])[C:5]([O:6][CH2:16][CH2:14][OH:15])=[CH:7][CH:8]=1)#[N:12]

Participants

4

Reactant 3

HCID 700Ethanolamine2×HCID 6342AcetonitrileHCID 10583428Methyl 5-cyano-2-hydroxybenzoate

Product 1

HCID 189971115-Cyano-(2-hydroxyethyl)salicylamide

Procedure

A solution of 9.7 g (0.547 mole) of 5-cyanosalicylic acid methyl ester (prepared as described in Chem. Pharm. Bull., 1984, 38, 4466-4477) in 15 ml of acetonitrile, was combined with 4.01 g (0.65 mole) of ethanolamine, and then heated at reflux for 24 hours. At the end of the 4th and 7th hours, two further portions of 1 g (0.016 mole) each of ethanolamine were added. At the end of the heating, the solution was evaporated to dryness under vacuum, taken up with ethyl acetate and washed with hydrochloric acid 1N and then with water. The organic layer was dried over sodium sulphate and concentrated to small volume. The formed solid was filtered and dried under vacuum yielding 9.2 g of 5-cyano-(2-hydroxyethyl)salicylamide. m.p. 144°-146° C. (acetonitrile).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. customAt the end of the heating, the solution was evaporated to dryness under vacuum
  4. washwashed with hydrochloric acid 1N
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated to small volume
  7. filtrationThe formed solid was filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-89f42e1be6a04a159f008a6dc178f94a
Source dataset
uspto-grants-1996_01
Patent number
US05480882

Reaction notes

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