Pyridine → HCID 14294179, compound

HRID 1381708Notes

Reaction equation

HRID 1381708 reaction equation
[NH:1]([C:3]([O:5][CH3:6])=[O:4])[NH2:2].N1C=CC=CC=1.[C:13]([CH2:17][C:18](Cl)=[O:19])([CH3:16])([CH3:15])[CH3:14]>ClCCl>[CH3:14][C:13]([CH3:16])([CH3:15])[CH2:17][C:18]([NH:2][NH:1][C:3]([O:5][CH3:6])=[O:4])=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 80519Methyl carbazateHCID 815143,3-Dimethylbutanoyl chloride

Product 1

HCID 14294179HCID 14294179, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 65.5 g of hydrazinecarboxylic acid, methyl ester, 150 ml of dry pyridine and 500 ml of dry dichloromethane was stirred at 0° C. and 100 g of distilled t-butylacetyl chloride was added dropwise. After 2 hours at 0°-5° C. the solvent was removed in vacuo. The residue was taken up in 1.2 liters of ethyl acetate, washed with saturated sodium chloride and filtered through a bed of hydrous magnesium silicate with additional ethyl acetate. The filtrate was concentrated and the solid recrystallized from diisopropyl ether, giving 130 g of 2-(3,3-dimethyl-l-oxobutyl)hydrazinecarboxylic acid, methyl ester as white platelets, mp 83°-84.5° C.

Workup

  1. customAfter 2 hours at 0°-5° C. the solvent was removed in vacuo
  2. washwashed with saturated sodium chloride
  3. filtrationfiltered through a bed of hydrous magnesium silicate with additional ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customthe solid recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-df9b3ecd733741fc9cf35e35a94c293a
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

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