4-Nitrobenzoic Acid → HCID 178525746, compound

HRID 1269784Notes

Reaction equation

HRID 1269784 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:4][CH2:3]1.[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:1][C@H:2]2[CH2:3][CH2:4][C@@H:5]([N:8]3[C:9](=[O:18])[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:16]3=[O:17])[CH2:6][CH2:7]2)=[O:27])=[CH:29][CH:30]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 66777355Diethylazodicarboxylate tolueneHCID 178515017HCID 178515017, compound

Product 1

HCID 178525746HCID 178525746, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-2-(4-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione (359 mg, 1.46 mmol) in tetrahydrofuran (15 ml) were added p-nitrobenzoic acid (245 mg, 1.46 mmol), triphenylphosphine (422 mg, 1.61 mmol) and a 40%-diethyl azodicarboxylate/toluene solution (0.73 ml, 1.61 mmol) at 0° C., and stirred at 0° C. for 30 minutes and then at room temperature for 3 hours. The reaction solution was concentrated and the resulting residue was dissolve in a mixed solution of ethanol (10 ml) and diisopropyl ether (10 ml) at 60° C. Then, the resulting solution was allowed to cool and the crystals formed were filtered under reduced pressure to obtain cis-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)cyclohexyl 4-nitrobenzoate (427 mg, 74%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe resulting residue was dissolve in a mixed solution of ethanol (10 ml) and diisopropyl ether (10 ml) at 60° C
  3. temperatureto cool
  4. customthe crystals formed
  5. filtrationwere filtered under reduced pressure

Sources & evidence

ORD record
ord-e224fe3b4a0e4177afd34637aa3bde91
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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