Acetic Anhydride → 1-Acetamido-7-naphthol

HRID 895218

反応式

HRID 895218 の反応式
[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

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 83588-Amino-2-naphthalenol

生成物 1

HCID 809461-Acetamido-7-naphthol収率 93.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 8-amino-2-naphthol (149.1 g, 0.937 mol) in methanol (1L) 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/z202 (M+H)+.

後処理

  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

出典と根拠

ORDレコード
ord-731f0fa500514dc1b73c04d6529fad4f
出典データセット
uspto-grants-2005_07
特許番号
US06914074B2

関連ノート

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