Hydrazine hydrate (1:1) → HCID 62290634, compound

HRID 715387Notes

Reaction equation

HRID 715387 reaction equation
O.NN.[Cl:4][C:5]1[CH:6]=[C:7]([CH2:17][N:18]2C(=O)C3C(=CC=CC=3)C2=O)[CH:8]=[N:9][C:10]=1[O:11][CH2:12][C:13]([F:16])([F:15])[F:14]>CO>[Cl:4][C:5]1[CH:6]=[C:7]([CH2:17][NH2:18])[CH:8]=[N:9][C:10]=1[O:11][CH2:12][C:13]([F:14])([F:15])[F:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67508616HCID 67508616, compound

Product 1

HCID 62290634HCID 62290634, compoundYield 111.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Hydrazine monohydrate (0.04 mL, 0.84 mmol) is added to a solution of 2-((5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isoindoline-1,3-dione (210 mg, 0.56 mmol, Step-3) in methanol (10 mL) and stirred for 20 hours at 50° C. After removal of the solvent, the residue is poured into 2 M aqueous sodium hydroxide solution (10 mL) and extracted with DCM (30 mL×3) and dried over sodium sulfate, and concentrated in vacuo to give 0.15 g (>99% yield) of the title compound as colorless oil. This material is used for the next reaction without further purification.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue is poured into 2 M aqueous sodium hydroxide solution (10 mL)
  3. extractionextracted with DCM (30 mL×3)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b2c90d334a44efbbe4a515b7d19ebb4
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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