Hydrochloric Acid → 3,4,5,6-Tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid N'-pentanoyl-hydrazide

HRID 269733Notes

Reaction equation

HRID 269733 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[C:7]([NH:13][NH2:14])(=[O:12])[CH2:8][CH2:9][CH2:10][CH3:11].[CH3:15][N:16]1[CH2:20][CH2:19][CH2:18][C:17]1=O.Cl>ClCCl.CN(C)C=O.O>[C:7]([NH:13][NH:14][C:1]([CH:2]1[CH2:19][CH2:20][N:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:15][N:16]=2)[CH2:17][CH2:18]1)=[O:5])(=[O:12])[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 65578Oxalyl chlorideHCID 93202Valerohydrazide

Product 1

HCID 235440703,4,5,6-Tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid N'-pentanoyl-hydrazideYield 30.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

The carboxylic acid from Preparation 2 (1.5 g, 7.3 mmol) was suspended in dichloromethane (40 mL) containing N,N-dimethylformamide (2 drops) and oxalyl chloride (1.27 mL, 14 mmol) in dichloromethane (5 mL) was added dropwise. The mixture was stirred for 5 hours at room temperature and then evaporated under reduced pressure. The residue was suspended in hexane and evaporate (3×20 mL). The residue was dissolved in dichloromethane and cooled to 0° C. and pentanoic acid hydrazide (1.7 g, 14.6 mmol) was added. 1-Methyl-pyrrolidin-2one (1.6 mL, 14.6 mmol) in dichloromethane (10 mL) was added drop wise and the mixture was stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure and the residue was triturated with diethyl ether. The material obtained was dissolved in water and acidified to pH 2 by addition of 2N hydrochloric acid. The acidic solution was filtered and the filtrate was washed with ethyl acetate (3×20 mL) then basified with sodium carbonate. The solid formed was triturated with diethyl ether and isolated by filtration to give the title compound as a white solid (0.68 g).

Workup

  1. additionwas added dropwise
  2. customevaporated under reduced pressure
  3. customevaporate (3×20 mL)
  4. dissolutionThe residue was dissolved in dichloromethane
  5. temperaturecooled to 0° C.
  6. stirringthe mixture was stirred at room temperature for 16 hours
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was triturated with diethyl ether
  9. customThe material obtained
  10. filtrationThe acidic solution was filtered
  11. washthe filtrate was washed with ethyl acetate (3×20 mL)
  12. customThe solid formed
  13. customwas triturated with diethyl ether
  14. customisolated by filtration

Sources & evidence

ORD record
ord-51cfafd6d26a4f528f49b7ab12cf7290
Source dataset
uspto-grants-2008_11
Patent number
US07449462B2

Reaction notes

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