Acetic Anhydride → 1-Acetamido-7-naphthol

HRID 260667

Reaction equation

HRID 260667 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[OH:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][CH:3]=[C:2]2[NH:1][C:13](=[O:15])[CH3:14])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 83588-Amino-2-naphthalenol

Product 1

HCID 809461-Acetamido-7-naphtholYield 98.3%

Procedure

100 g (0.55 mol) of 8-aminonaphth-2-ol are poured into 125 ml (135.25 g or 1.325 mol) of acetic anhydride cooled in an ice bath, and the mixture is stirred under cold conditions for 1 h. The mixture obtained is poured into 375 ml of ice-water and stirred for several hours. The violet solid is collected by filtration, washed three times with 30 ml of diethyl ether and dried under reduced pressure. 108.8 g of a product melting point: 193°-195° C. are obtained which is used as it is in the following step.

Workup

  1. temperaturecooled in an ice bath
  2. customThe mixture obtained
  3. stirringstirred for several hours
  4. filtrationThe violet solid is collected by filtration
  5. washwashed three times with 30 ml of diethyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-13936575bfc34ea29975b969b0f98d9f
Source dataset
uspto-grants-1996_06
Patent number
US05530002

Linked notes

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