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

HRID 712244ノート

反応式

HRID 712244 の反応式
[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

参加物

5

反応物 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 409963Ethyl 4-aminocyclohexanecarboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-581955aa14894ae99c3fa801f20e347b
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

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