Methyl 4-hydrazinylbenzoate → Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate

HRID 574425Notes

Reaction equation

HRID 574425 reaction equation
[NH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[NH2:2].Br[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[N:20][CH:21]=1>C(N(CC)CC)C>[CH3:22][C:19]1[N:20]=[CH:21][C:16]([CH2:15][CH2:14][N:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=2)[NH2:2])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 408928Methyl 4-hydrazinylbenzoateHCID 533058565-(2-Bromoethyl)-2-methylpyridine

Product 1

HCID 68735268Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoateYield 28.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Methyl 4-hydrazinylbenzoate (1 g, 0.005 moles) and 5-(2-bromoethyl)-2-methylpyridine (1 g, 0.005 moles) was taken up in 2.1 mL of triethylamine and stirred at RT for 1 hr. The reaction was then heated at 100 degrees C., overnight. LCMS analysis of the reaction mixtures shows the formation of product. Reaction mixture was concentrated, water (20 mL) was added to the reaction mixture and the mixture extracted with ethyl acetate. The crude product was dissolved in ethyl acetate and purified by column chromatography using neutral alumina, using 100% ethyl acetate as the eluent. After chromatography 400 mg of Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate was obtained, 28.5% yield.

Workup

  1. temperatureThe reaction was then heated at 100 degrees C
  2. customovernight
  3. customLCMS analysis of the reaction mixtures
  4. customReaction mixture
  5. concentrationwas concentrated
  6. additionwater (20 mL) was added to the reaction mixture
  7. extractionthe mixture extracted with ethyl acetate
  8. dissolutionThe crude product was dissolved in ethyl acetate
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-0dae2e546baa499bbfa8e0983f242b07
Source dataset
uspto-grants-2015_05
Patent number
US09034880B2

Reaction notes

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