Water → N-(4-hydroxynaphthalen-1-yl)acetamide

HRID 1492127Notes

Reaction equation

HRID 1492127 reaction equation
O.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:13])=[CH:5][CH:4]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>C(O)C>[OH:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([NH:2][C:14](=[O:16])[CH3:15])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 178151-Amino-4-naphthol

Product 1

HCID 235848N-(4-hydroxynaphthalen-1-yl)acetamideYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 500 ml round bottom flask (fitted with a magnetic stirrer), a 50:50 mixture of water:ethanol was combined with 4-amino1-naphthol (20 g, 125 mmole) until the solid was completely dissolved. The solution was warmed to boiling, and to it was added acetic anhydride (14 g) and the resulting solution was stirred for 1 hour. Upon cooling, crystals of N-(4-hydroxy-1-naphthyl)acetamide (20 g, 79% yield) formed.

Workup

  1. customInto a 500 ml round bottom flask (fitted with a magnetic stirrer)
  2. dissolutionwas completely dissolved
  3. temperatureThe solution was warmed
  4. temperatureUpon cooling

Sources & evidence

ORD record
ord-9d36a4eb96e4449bbcd6f139e87e7d73
Source dataset
uspto-grants-1994_12
Patent number
US05372931

Reaction notes

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