Acetic Anhydride → 1-Acetamido-7-naphthol

HRID 1830665

Reaction equation

HRID 1830665 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]>CO>[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

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 83588-Amino-2-naphthalenol

Product 1

HCID 809461-Acetamido-7-naphtholYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-amino-2-naphthol (149.1 g, 0.937 mol) in methanol (1 L) was added acetic anhydride (93 mL, 0.984 mol). The reaction was refluxed for 90 minutes and cooled to room temperature. The solvent was removed and the residue was filtered through a plug of silica with ethyl acetate. The solvent was removed to yield 175.8 g (93%) of the title compound as a dark purple solid. An analytical sample was further purified by reverse phase preparative HPLC to yield a pink solid: mp 161–162° C.; 1H NMR (DMSO-d6):δ 2.15 (3H, s), 7.09 (1H, dd, J=1.95 Hz, J=8.79 Hz), 7.20–7.26 (2H, m), 7.49 (1H, d, J=7.31 Hz), 7.63 (1H, d, J=8.11 Hz), 7.77 (1H, d, J=8.81 Hz), 9.76 (1H, s), 9.79 (1H, s); MS (ESI) m/z 202 (M+H)+.

Workup

  1. temperatureThe reaction was refluxed for 90 minutes
  2. customThe solvent was removed
  3. filtrationthe residue was filtered through a plug of silica with ethyl acetate
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-a947f87c4bfc49999d6fb7c85c230f44
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Linked notes

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