Hydroxylamine → 7-(4-Hydroxyphenyl)-benzofuran-5-carbaldehyde oxime

HRID 1372169노트

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HRID 1372169 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[O:15][CH:14]=[CH:13][C:12]=3[CH:11]=[C:10]([CH:17]=O)[CH:9]=2)=[CH:4][CH:3]=1.[NH2:19][OH:20].CO.N1C=CC=CC=1>CCOCC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[O:15][CH:14]=[CH:13][C:12]=3[CH:11]=[C:10]([CH:17]=[N:19][OH:20])[CH:9]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 787HydroxylamineHCID 887MethanolHCID 1049PyridineHCID 210717937-(4-Hydroxyphenyl)-benzofuran-5-carbaldehyde

생성물 1

HCID 854277617-(4-Hydroxyphenyl)-benzofuran-5-carbaldehyde oxime

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
68 °C

실험 절차

To a 25 ml round bottom flask was added 7-(4-hydroxyphenyl)-benzofuran-5-carbaldehyde (400 mg, 1.68 mmol), hydroxylamine hydrochlorode (234 mg, 3.36 mmol), anhydrous MeOH (10.4 ml), and anhydrous pyridine (0.272 ml, 3.36 mmol). The reaction was then heated to 68° C. and the reaction was brought to reflux for 1 h. The reaction was then cooled to room temperature, dilute with ether, and the layers separated. The ether layer was washed with water, dried over anhydrous Na2SO4, passed through a silica plug, and concentrated to 410 mg (96%) product as a yellow solid. The crude material was pure by 1H NMR (−4% cis isomer was detected) and LC-MS (one peak): mp 192–194° C. 1H NMR (300 MHz, DMSO-d6): δ 6.92 (2H, d, J=8.6 Hz), 7.05 (1H, d, J=2.2 Hz), 7.69–7.72 (3H, m), 7.79 (1H, d, J=1.4 Hz), 8.09 (1H, d, J=1.1 Hz), 8.27 (1H, s), 9.74 (1H, s), 11.14 (1H, s); MS (ESI) m/z 254 ([M+H]+).

후처리

  1. temperatureto reflux for 1 h
  2. temperatureThe reaction was then cooled to room temperature
  3. customthe layers separated
  4. washThe ether layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated to 410 mg (96%) product as a yellow solid

출처 및 근거

ORD 기록
ord-a25e9452d262461cbe123640c7728b01
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157491B2

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