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

HRID 712244Notes

Reaction equation

HRID 712244 reaction equation
[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

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 409963Ethyl 4-aminocyclohexanecarboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-581955aa14894ae99c3fa801f20e347b
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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