2-[(3-Bromo-6-quinolinyl)methyl]-1H-isoindole-1,3(2H)-dione → HCID 58190486, compound

HRID 1892419Notes

Reaction equation

HRID 1892419 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][N:13]1C(=O)C3C(=CC=CC=3)C1=O)=[CH:7][CH:6]=2>CO.O.NN>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][NH2:13])=[CH:7][CH:6]=2

Participants

4

Reactant 1

HCID 581905432-[(3-Bromo-6-quinolinyl)methyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 58190486HCID 58190486, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

A solution of 2-(3-Bromo-quinolin-6-ylmethyl)-isoindole-1,3-dione (635 g, 1.73 mmol) in 15 mL of methanol and 1 mL of hydrazine monohydrate was heated at 80° C. for 2 h. After cooling, the solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient to afford the title compound. LCMS (method A): [MH]+=237/239, tR=2.795 min.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient

Sources & evidence

ORD record
ord-35bd4764d4e04b8692688c1c445ea627
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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