2-Hydrazinyl-4-methylpyridine → N-[(E)-[8-[tert-butyl(dimethyl)silyl]oxyquinolin-2-yl]methylideneamino]-4-methylpyridin-2-amine

HRID 876464Notes

Reaction equation

HRID 876464 reaction equation
[NH:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1)[NH2:2].[Si:10]([O:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]=[C:25]([CH:28]=O)[CH:24]=[CH:23]2)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>CCO>[Si:10]([O:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]=[C:25](/[CH:28]=[N:2]/[NH:1][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1)[CH:24]=[CH:23]2)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 122667392-Hydrazinyl-4-methylpyridineHCID 585670828-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde

Product 1

HCID 67230767N-[(E)-[8-[tert-butyl(dimethyl)silyl]oxyquinolin-2-yl]methylideneamino]-4-methylpyridin-2-amineYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydrazinyl-4-methylpyridine (0.280 g, 2.27 mmol) and 8-(tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde (0.653 g, 2.27 mmol) were suspended in EtOH (6 mL) and stirred overnight at ambient temperature. The resulting suspension was filtered and the solid was washed with cold EtOH and dried in vacuo to provide the title compound (0.720 g; 81%).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solid was washed with cold EtOH
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e7503f31b6404425bd5283a3e81d818b
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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