2-Hydrazinyl-4-(2-methoxyethoxy)pyridine → 8-(Tert-butyldimethylsilyloxy)-2-((2-(4-(2-methoxyethoxy)pyridin-2-yl)hydrazono)methyl)quinoline

HRID 876402

Reaction equation

HRID 876402 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 672297698-(Tert-butyldimethylsilyloxy)-2-((2-(4-(2-methoxyethoxy)pyridin-2-yl)hydrazono)methyl)quinolineYield 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-233ef1564fe24ea497bc7dbca98f0423
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Linked notes

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