Acetic Anhydride → 1-Acetamido-7-naphthol

HRID 895218

반응식

HRID 895218 반응식
[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

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 83588-Amino-2-naphthalenol

생성물 1

HCID 809461-Acetamido-7-naphthol수율 93.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-731f0fa500514dc1b73c04d6529fad4f
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06914074B2

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