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

HRID 6912Notes

Reaction equation

HRID 6912 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 1 (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 drop wise. The mixture was stirred for 5 hours at room temperature and then was evaporated under reduced pressure. The residue was suspended in hexane and evaporated (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-2-one (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 pH2 by addition of 2N hydrochloric acid. The acidic solution 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 drop wise
  2. customwas evaporated under reduced pressure
  3. customevaporated (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 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-ada1b54a83b344aea2f34e86236cf6ac
Source dataset
uspto-grants-2006_08
Patent number
US07084145B2

Reaction notes

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