Hydrochloric Acid → N'-methyl(tert-butoxy)carbohydrazide

HRID 1461879Notes

Reaction equation

HRID 1461879 reaction equation
[CH3:1][C:2]([CH3:20])([O:4][C:5]([NH:7][N:8](C(OCC1C=CC=CC=1)=O)[CH3:9])=[O:6])[CH3:3].Cl>CO.[Pd]>[CH3:1][C:2]([CH3:20])([O:4][C:5]([NH:7][NH:8][CH3:9])=[O:6])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 110332501-Benzyl 2-tert-butyl 1-methylhydrazine-1,2-dicarboxylate

Product 1

HCID 15671306N'-methyl(tert-butoxy)carbohydrazideYield 71.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-[(1,1-dimethylethoxy)carbonyl]-2-[(phenylmethoxy)carbonyl]-2-methylhydrazine (15.0 g, 53. mmole) in 100 ml of methanol containing 4.9 ml of concentrated hydrochloric acid was hydrogenated at 1 atm in the presence of 3.0 g of 10% palladium-on-charcoal catalyst for 1 hour. The catalyst was filtered and the solvents were removed in vacuo. The residue was dissolved in water, the pH adjusted to 8.0 with sodium hydroxide and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and evaporated to give 5.6 g of the title compound as a colorless solid, m.p. 50° C.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-a0c5cdcdbb184738b2033ac1bae4d638
Source dataset
uspto-grants-1991_12
Patent number
US05077432

Reaction notes

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