Ammonia → N-(6-Hydroxy-2-naphthyl)acetamide

HRID 1492126Notes

Reaction equation

HRID 1492126 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[NH3:13].[O:14]1CC[CH2:16][CH2:15]1>>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([NH:13][C:15](=[O:14])[CH3:16])[CH:11]=[CH:10]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 3014514N-(6-Hydroxy-2-naphthyl)acetamideYield 63%

Conditions

Temperature
80 °C

Procedure

Into a high pressure reaction vessel (fitted for shaking), tetrahydrofuran (200 ml) was combined with 6-bromo-2-naphthol. The reaction vessel was then charged with gaseous ammonia (800 psi, 56.2 kg/cm2) and warmed to 80° C. for 3 days. The resulting solution was removed by reduced pressure and some of the solid precipitate 6-amino-2-napthol (10 g) was placed (without further purification) into a 500 ml round bottom flask). The solid was completely dissolved into a 50:50 mixture of water:ethanol. The resulting solution was warmed to boiling and acetic anhydride (7 g) was added. After 1 hour of continuous stirring, the solution was cooled and crystals of N-(6-hydroxy-2-naphthyl)acetamide formed (8 g, 63% yield).

Workup

  1. customThe resulting solution was removed by reduced pressure
  2. custom(without further purification) into a 500 ml round bottom flask)
  3. dissolutionThe solid was completely dissolved into a 50:50 mixture of water
  4. temperatureThe resulting solution was warmed
  5. additionacetic anhydride (7 g) was added
  6. temperaturethe solution was cooled

Sources & evidence

ORD record
ord-2da7006da1a14ae68ddc98afaa98924e
Source dataset
uspto-grants-1994_12
Patent number
US05372931

Reaction notes

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