Hydrazine → HCID 66738290, compound

HRID 1640893Notes

Reaction equation

HRID 1640893 reaction equation
NN.[F:3][C:4]1[N:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)=[C:6]([I:24])[CH:5]=1>C(O)C>[F:3][C:4]1[N:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH2:13])=[C:6]([I:24])[CH:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66738229HCID 66738229, compound

Product 1

HCID 66738290HCID 66738290, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add hydrazine (70 mg, 2.12 mmol) to a solution of 2-[2-(6-fluoro-4-iodo-pyridin-3-yloxy)-ethyl]-isoindole-1,3-dione (440 mg, 1.06 mmol) in ethanol (10 mL). Stir the solution at RT overnight. Filter to remove the solid and concentrate the filtrate to a light yellow solid. Purify by column chromatography (10% 2 M ammonia in methanol in methylene chloride) to afford the title compound as a light yellow oil (250 mg, 83.8%). 1H NMR (400 MHz, CD3CN) δ 2.12 (s, 2H), 3.03 (t, J=5.2 Hz, 2H), 4.10 (t, J=5.2 Hz, 2H), 7.47 (d, J=4.0 Hz, 1H), 7.69 (d, J=2.0 Hz, 1H).

Workup

  1. filtrationFilter
  2. customto remove the solid
  3. concentrationconcentrate the filtrate to a light yellow solid
  4. customPurify by column chromatography (10% 2 M ammonia in methanol in methylene chloride)

Sources & evidence

ORD record
ord-65335176e6fe4656a9ff8e43600bb19a
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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