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

HRID 2035555Notes

Reaction equation

HRID 2035555 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH:19]=O)[CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[I:21][C:22]1[CH:27]=[CH:26][NH:25]/[C:24](=[N:28]\[NH2:29])/[CH:23]=1>C(Cl)Cl>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16](/[CH:19]=[N:29]/[N:28]=[C:24]1\[NH:25][CH:26]=[CH:27][C:22]([I:21])=[CH:23]\1)[CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 534028972-Hydrazinyl-4-iodopyridineHCID 585670828-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde

Product 1

HCID 178455024N-[(E)-[8-[tert-butyl(dimethyl)silyl]oxyquinolin-2-yl]methylideneamino]-4-iodopyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 8-(tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde (3.21 g, 11.2 mmol) in DCM (30 mL) was added (Z)-1-(4-iodopyridin-2(1H)-ylidene)hydrazine (3.15 g, 13.4 mmol). The reaction was stirred for 1 hour, affording a yellow precipitate, which was collected by filtration and used without further purification in the next step.

Workup

  1. customaffording a yellow precipitate, which
  2. filtrationwas collected by filtration
  3. customused without further purification in the next step

Sources & evidence

ORD record
ord-4ead848e64ad49ceb87385ce2a7e726d
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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