Methylhydrazine → HCID 22286203, compound

HRID 2218453Notes

Reaction equation

HRID 2218453 reaction equation
[CH3:1][C:2]1([CH3:22])[O:6][CH:5]([CH2:7][O:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[C:4]([CH3:21])([CH3:20])[O:3]1.CNN>ClCCl>[CH3:1][C:2]1([CH3:22])[O:6][CH:5]([CH2:7][O:8][NH2:9])[C:4]([CH3:21])([CH3:20])[O:3]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 22286604HCID 22286604, compound

Product 1

HCID 22286203HCID 22286203, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethoxy)-isoindole-1,3-dione (0.158 g, 0.52 mmol) was dissolved in dichloromethane (3 mL), cooled to 0° C., and charged with methylhydrazine (30 μL, 0.57 mmol). The ice bath was removed and the reaction was allowed to stir at ambient temperature for 1 hour. The reaction mixture was diluted with diethylether and the solids were filtered off and filtrate concentrated in vacuo to afford O-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine as a yellow oil (0.042 g, 46%). 1H NMR (400 MHz; DMSO-d6) δ 6.06 (bs, 2H), 3.84-3.87 (m, 1H), 3.50-3.59 (m, 2H), 1.26 (s, 3H), 1.19 (s, 3H), 1.16 (s, 3H), 0.94 (s, 3H); MS (APCI+)=176.9.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction mixture was diluted with diethylether
  3. filtrationthe solids were filtered off
  4. concentrationfiltrate concentrated in vacuo

Sources & evidence

ORD record
ord-86811abb96aa4f31b0c73318fca6dfde
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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