Methylhydrazine → tert-butyl N-(2-(aminooxy)ethyl)carbamate

HRID 1897402Notes

Reaction equation

HRID 1897402 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][O:10][N:11]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].CNN>C(Cl)Cl>[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][O:10][NH2:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6061Methylhydrazine2×HCID 18929164tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

Product 1

HCID 15610443tert-butyl N-(2-(aminooxy)ethyl)carbamateYield 102.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(1,3-dioxo-1,3-dihydroisoindol-2-yloxy)-ethyl]-carbamic acid tert-butyl ester (0.842 g, 2.749 mmol) was dissolved in 20 ml of CH2Cl2 and methylhydrazine (150 μL, 2.776 mmol) was added at room temperature. As soon as methylhydrazine was added, a white precipitate was formed. The reaction was stirred at room temperature for 72 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to provide 0.496 g of a viscous oil (102% yield). The crude material was used without further purification.

Workup

  1. customa white precipitate was formed
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6673407c9f2843aa9a6c1dc63de30820
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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