Triethylamine → 1-(4-Methylphenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine
Reaction equation
C(N(CC)CC)C.Cl.[C:9]1([CH3:17])[CH:14]=[CH:13][C:12]([NH:15][NH2:16])=[CH:11][CH:10]=1.Br[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[N:25][CH:26]=1>>[CH3:27][C:24]1[N:25]=[CH:26][C:21]([CH2:20][CH2:19][N:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:17])=[CH:10][CH:11]=2)[NH2:16])=[CH:22][CH:23]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
The title compound was prepared by General Method 1. Triethylamine (13.0 mL, 94.5 mmol) was added dropwise to p-tolylhydrazine hydrochloride (5.0 g, 31.5 mmol) over a period of 5-10 min. The reaction mixture was stirred for additional 10 min. 5-(2-bromoethyl)-2-methylpyridine (6.3 g, 31.5 mmol) was added dropwise at 25° C. over a period of 10-15 min. The reaction mixture was stirred at RT for 1 h and the subsequently heated at 90° C. for 2-3 h at which point the reaction was found complete by TLC and LC-MS. Reaction mixture was concentrated under reduced pressure and diluted with water (50 mL) and extracted with ethyl acetate (100 mL×2). The organic layer was separated, dried (Na2SO4) and concentrated to obtain crude product as dark brown oil (16.7 g). Purification of crude product by column chromatography (silica gel, 100-200 mesh, eluent: 0-40% ethyl acetate-Hexane) furnished 1.92 g of pure product as brown liquid. Yield: 25%.
Workup
- stirringThe reaction mixture was stirred at RT for 1 h
- customReaction mixture
- concentrationwas concentrated under reduced pressure
- additiondiluted with water (50 mL)
- extractionextracted with ethyl acetate (100 mL×2)
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customto obtain crude product as dark brown oil (16.7 g)
Sources & evidence
- ORD record
- ord-51c3cf4545c54e64843c7f22413a35d9
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338447B2
Reaction notes
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