Phthalic Anhydride → Ethyl 4-(1,3-dioxoisoindolin-2-yl)cyclohexanecarboxylate

HRID 712244노트

반응식

HRID 712244 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.CCN(CC)CC.[C:20]1(=O)[O:25][C:23](=[O:24])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12>C1(C)C=CC=CC=1>[O:24]=[C:23]1[C:22]2[C:21](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20](=[O:25])[N:1]1[CH:2]1[CH2:3][CH2:4][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1

참가 물질

5

반응물 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 409963Ethyl 4-aminocyclohexanecarboxylate

생성물 1

HCID 4082309Ethyl 4-(1,3-dioxoisoindolin-2-yl)cyclohexanecarboxylate수율 34.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of ethyl 4-aminocyclohexanecarboxylate (0.50 g, 2.92 mmol) in toluene (10 mL) was added Et3N (1.02 mL, 7.30 mmol) and phthalic anhydride (0.56 g, 3.80 mmol) and the mixture refluxed for 6-8 h using dean-stark apparatus to remove water. After completion of the reaction (by TLC), the solvent was evaporated under reduced pressure, water (50 mL) added and stirred for 30 min at rt. The solid material thus obtained was collected by filtration under vacuum and dried to obtain the desired product as off-white solid (0.30 g, 34%). 1H NMR (DMSO-d6): δ 7.84 (s, 4H), 4.19 (q, J=7.20 Hz, 2H), 3.71 (m, 1H), 2.71 (m, 1H), 2.06 (m, 2H), 1.90 (m, 2H), 1.69 (m, 2H), 1.60 (m, 2H), and 1.23 (t, J=7.20 Hz, 3H).

후처리

  1. temperaturethe mixture refluxed for 6-8 h
  2. customto remove water
  3. customAfter completion of the reaction (by TLC)
  4. customthe solvent was evaporated under reduced pressure, water (50 mL)
  5. additionadded
  6. customThe solid material thus obtained
  7. filtrationwas collected by filtration under vacuum
  8. customdried

출처 및 근거

ORD 기록
ord-581955aa14894ae99c3fa801f20e347b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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