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

HRID 339663

Reaction equation

HRID 339663 reaction equation
[NH:1]([C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][O:12][CH3:13])[CH:6]=[CH:5][N:4]=1)[NH2:2].[Si:14]([O:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[C:29]([CH:32]=O)[CH:28]=[CH:27]2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CCO>[Si:14]([O:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[C:29](/[CH:32]=[N:2]/[NH:1][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][O:12][CH3:13])[CH:6]=[CH:5][N:4]=1)[CH:28]=[CH:27]2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 552790432-Hydrazinyl-4-(2-methoxyethoxy)pyridineHCID 585670828-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde

Product 1

HCID 173055441N-[(E)-[8-[tert-butyl(dimethyl)silyl]oxyquinolin-2-yl]methylideneamino]-4-(2-methoxyethoxy)pyridin-2-amineYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydrazinyl-4-(2-methoxyethoxy)pyridine (0.076 g, 0.415 mmol) and 8-(tert-butyldimethylsilyloxy) quinoline-2-carbaldehyde (0.119 g, 0.415 mmol) were heated to reflux in EtOH (2 mL) for 16 hours. After cooling to ambient temperature the reaction mixture was filtered and washed with EtOH to provide 105 mg (56%) of desired product as an orange solid.

Workup

  1. filtrationwas filtered
  2. washwashed with EtOH

Sources & evidence

ORD record
ord-54203cd3635c4e7f9b56a7890bb40afa
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Linked notes

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