Methyl 6-hydrazinylpyridine-3-carboxylate → methyl 6-[(2E)-2-[(8-tert-butylquinolin-2-yl)methylidene]hydrazinyl]pyridine-3-carboxylate

HRID 338848Notes

Reaction equation

HRID 338848 reaction equation
[NH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1)[NH2:2].[C:13]([C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]=[C:24]([CH:27]=O)[CH:23]=[CH:22]2)([CH3:16])([CH3:15])[CH3:14]>C(O)C>[C:13]([C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]=[C:24](/[CH:27]=[N:2]/[NH:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1)[CH:23]=[CH:22]2)([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 55280209Methyl 6-hydrazinylpyridine-3-carboxylateHCID 867074158-Tert-butylquinoline-2-carbaldehyde

Product 1

HCID 70983754methyl 6-[(2E)-2-[(8-tert-butylquinolin-2-yl)methylidene]hydrazinyl]pyridine-3-carboxylateYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 6-hydrazinylnicotinate (1.00 g, 5.98 mmol) and 8-tert-butylquinoline-2-carbaldehyde (1.28 g, 5.98 mmol) in absolute ethanol (20 mL) was stirred at ambient temperature for 4 hours. The solid that formed was collected by filtration, washed with ethanol (10 mL), ether (100 mL) and dried to give (E)-methyl 6-(2-((8-tert-butylquinolin-2-yl)methylene)hydrazinyl)nicotinate (1.78 g, 82.1%) as a solid.

Workup

  1. customThe solid that formed
  2. filtrationwas collected by filtration
  3. washwashed with ethanol (10 mL), ether (100 mL)
  4. customdried

Sources & evidence

ORD record
ord-735d9657b4344faca73df70a356e6432
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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