Hydrazine hydrate (1:1) → HCID 12571735, compound

HRID 1697442Notes

Reaction equation

HRID 1697442 reaction equation
O.NN.[Cl:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][N:10]2C(=O)C3=CC=CC=C3C2=O)=[CH:7][CH:6]=1>C(Cl)(Cl)Cl.CO>[Cl:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][NH2:10])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 153707352-(4-Chlorophenoxy)isoindoline-1,3-dione

Product 1

HCID 12571735HCID 12571735, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Hydrazine hydrate (0.56 mL, 12 mmol) was added to a solution of Example 3A (820 mg, 3.0 mmol) in chloroform (37 mL) and methanol (4 mL). The suspension was stirred at room temperature for 22 hours. Silica gel (10 g) was added, and the mixture was concentrated to dryness. The residue was applied to the top of a flash chromatography column and eluted with hexanes-ethyl acetate (80:20) to provide the title compound as the free amine. The residue was dissolved in ethanol (5 mL) and treated with HCl/dioxane (4M, 1 mL). The solution was heated at reflux and diluted with gradual addition of ethyl acetate (50 mL). The mixture was cooled to room temperature and filtered to provide the title compound as a hydrochloride salt. 1H NMR (300 MHz, CD3OD) δ 7.15-7.22 (m, 2 H), 7.42-7.49 (m, 2 H).

Workup

  1. additionSilica gel (10 g) was added
  2. concentrationthe mixture was concentrated to dryness
  3. washeluted with hexanes-ethyl acetate (80:20)

Sources & evidence

ORD record
ord-d5b0d20dac0849c6ae4cb41d7105fad4
Source dataset
uspto-grants-2012_04
Patent number
US08163915B2

Reaction notes

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