Phthaloyl chloride → 2-[(1R)-1,2,3,4-Tetrahydro-1-naphthalenyl]-1H-isoindole-1,3(2H)-dione

HRID 1363218Notes

Reaction equation

HRID 1363218 reaction equation
[C@H:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:12](Cl)(=[O:22])[C:13]1[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:15](Cl)=[O:16]>C1COCC1.C(Cl)Cl>[C@H:1]1([N:11]2[C:15](=[O:16])[C:14]3[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:12]2=[O:22])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6955Phthaloyl chlorideHCID 70580721-Aminotetralin, (R)-

Product 1

HCID 70160162-[(1R)-1,2,3,4-Tetrahydro-1-naphthalenyl]-1H-isoindole-1,3(2H)-dioneYield 73.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-1,2,3,4-tetrahydro-1-naphthylamine (6.0 g) in THF (150 mL) at 0° C. was added TEA (18.5 mL) and phthaloyl chloride (8.2 g), and the resultant mixture was stirred at room temperature overnight and 70° C. for 3 h. The mixture was diluted with CH2Cl2, washed with saturated NaHCO3, dried over MgSO4, and concentrated in vacuo. The resulting crude was chromatographed on silica gel (EtOAc/hexane, 5/95 to 30/70) to afford 8.2 g of the title compound.

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude was chromatographed on silica gel (EtOAc/hexane, 5/95 to 30/70)

Sources & evidence

ORD record
ord-50b87edec5534f438f9fc6b03fb222c4
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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