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

HRID 2035628Notes

Reaction equation

HRID 2035628 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-a644c984bf624698829627216e52a21a
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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