Ammonium Chloride → 5-Benzyloxy-2-(4-benzyloxyphenyl)isoindoline

HRID 853799Notes

Reaction equation

HRID 853799 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[C:20](=O)[N:19]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:27][CH:26]=1)[C:18]2=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[NH4+]>C1COCC1>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[CH2:20][N:19]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:27][CH:26]=1)[CH2:18]2)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 694715505-Benzyloxy-2-(4-benzyloxyphenyl)isoindoline-1,3-dione

Product 1

HCID 694728565-Benzyloxy-2-(4-benzyloxyphenyl)isoindolineYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension containing LiAlH4 (0.133 g) in THF (10 mL) under nitrogen atmosphere was added 5-benzyloxy-2-(4-benzyloxyphenyl)isoindoline-1,3-dione (0.435 g) in THF (15 mL) dropwise. The reaction was stirred at room temperature for 30 min, poured into cold, saturated ammonium chloride (100 mL) and extracted with ethyl acetate (2×75 mL). The organic layer was washed with brine and dried over MgSO4. After evaporation of the solvent, the residue was dried under high vacuum yielding the title compound (0.4 g) as a brown solid. 1H NMR (DMSO-d6): 7.45-7.31 (m, 13H), 6.70 (d, 2H, J=8.5 Hz), 6.51 (d, 2H, J=8.5 Hz), 5.12 (m, 4H), 4.41 (m, 4H); MS: 408 (MH+).

Workup

  1. extractionextracted with ethyl acetate (2×75 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customAfter evaporation of the solvent
  5. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-31f4755fda8c45eda2ba0e2f03d3f9a1
Source dataset
uspto-grants-2007_08
Patent number
US07256201B2

Reaction notes

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