2-(3-Bromo-quinolin-6-ylmethyl)-isoindole-1,3-dione → (3-Bromoquinolin-6-yl)methanamine
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]=2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- temperatureAfter cooling
- customthe solvent was removed in vacuo
- 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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