2-Naphthol → (2-(Naphthalen-2-yloxy)ethyl)acetamide

HRID 518943

반응식

HRID 518943 반응식
[CH3:1][C:2]1[O:3]CC[N:6]=1.[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[OH:17].[C:18](OCC)(=O)[CH3:19]>>[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[O:17][CH2:18][CH2:19][CH2:1][C:2]([NH2:6])=[O:3]

참가 물질

4

반응물 3

HCID 86632-Naphthol2회HCID 8857Ethyl AcetateHCID 707132-Methyl-2-oxazoline2회

생성물 1

HCID 82041146(2-(Naphthalen-2-yloxy)ethyl)acetamide

반응 조건

온도
70 °C

실험 절차

A 3-neck round bottom flask was charged with 2-methyl-2-oxazoline (5.9 mL, 69.4 mmol) followed by 2-naphthol (10.0 g, 69.4 mmol) at room temperature. The resulting mixture was heated to reflux and stirred for 6 h. Reaction was monitored by TLC analysis. Additional 2-methyl-2-oxazoline (2.5 mL, 29.4 mmol) was added to ensure complete conversion of the 2-naphthol and the reaction mixture was heated to reflux for 16 additional hours. The reaction mixture was cooled to 70° C. then poured into ethyl acetate (100 mL) and stirred for 15 min. The resulting slurry was filtered and washed with ethyl acetate (25 mL). The filter cake was further dried under vacuum to afford -(2-(naphthalen-2-yloxy)ethyl)acetamide as an off white solid (12.35 g, 77.7% yield). 1H NMR (DMSO-d6, 400 MHz) δ 8.179-8.126 (m, 1H), 8.84-7.79 (m, 3H), 7.7.48-7.43 (m, 1H), 7.37-7.32 (m, 2H), 7.18 (dd, j=2.59 Hz, 8.97 Hz, 1H) 4.11 (t, j=5.66, 2H), 3.48 (q, j=5.90 Hz, 2H), 1.85 (s, 3H).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. customReaction
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux for 16 additional hours
  6. stirringstirred for 15 min
  7. filtrationThe resulting slurry was filtered
  8. washwashed with ethyl acetate (25 mL)
  9. customThe filter cake was further dried under vacuum

출처 및 근거

ORD 기록
ord-bf38e48ca1c144df9fb40148915f6792
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115237B2

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