Hydrazine → 2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-ethylamine

HRID 228954Notes

Reaction equation

HRID 228954 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1C(=O)C3C(=CC=CC=3)C1=O)[N:9]=[CH:8][CH:7]=[C:6]2[O:27][C:28]1[C:29]([CH3:38])=[N:30][C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2.NN>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][NH2:16])[N:9]=[CH:8][CH:7]=[C:6]2[O:27][C:28]1[C:29]([CH3:38])=[N:30][C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 577565432-{2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-ethyl}-isoindole-1,3-dione2×

Product 1

HCID 577563932-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-ethylamineYield 107.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-ethyl}-isoindole-1,3-dione (compound 367) (20 mg) was dissolved in N,N-dimethylformamide (2 ml) to prepare a solution, hydrazine (13 mg) was added to the solution, and the mixture was stirred at room temperature for 4 hr. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (16 mg, yield 98%).

Workup

  1. additionwas added to the solution
  2. customThe solvent was removed by distillation under the reduced pressure
  3. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-3efc48f13c4f42dca521496b34ce3b66
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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