Methylhydrazine → N-ethyl(tert-butoxy)carbohydrazide

HRID 1908026Notes

Reaction equation

HRID 1908026 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[N:12]([CH2:20][CH3:21])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].CNN>C1COCC1>[CH2:20]([N:12]([C:13]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:19])[NH2:3])[CH3:21]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 58180562Tert-butyl (1,3-dioxoisoindolin-2-yl)(ethyl)carbamate

Product 1

HCID 57517432N-ethyl(tert-butoxy)carbohydrazideYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 1,3-dioxoisoindolin-2-yl(ethyl)-carbamate (790 mg, 2.7 mmol) in THF (16 mL) was cooled to 0° C. and methylhydrazine (250 μL, 4.8 mmol) was added. The reaction mixture was warmed to room temperature and was stirred until all starting material was consumed. The mixture was filtered through a pad of Celite and the solvent was evaporated. The residue was purified by column chromatography (0-10% methanol in dichloromethane) to afford tert-butyl 1-ethylhydrazinecarboxylate (320 mg, 74%). Retention time: 1.13 minutes (3 min run).

Workup

  1. customwas consumed
  2. filtrationThe mixture was filtered through a pad of Celite
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography (0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1706ef128d9e43dfb66711aaa96d8784
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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