Methylhydrazine → O-(2,2-dimethyl-1,3-dioxan-5-yl)Hydroxylamine

HRID 2218450Notes

Reaction equation

HRID 2218450 reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][CH:5]([O:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:4][O:3]1.CNN>ClCCl>[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][CH:5]([O:8][NH2:9])[CH2:4][O:3]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 220256752-(2,2-Dimethyl-[1,3]dioxan-5-yloxy)-isoindole-1,3-dione

Product 1

HCID 22025693O-(2,2-dimethyl-1,3-dioxan-5-yl)HydroxylamineYield 106.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-(2,2-dimethyl-[1,3]dioxan-5-yloxy)-isoindole-1,3-dione (1.72 g, 6.20 mmol) in dichloromethane (15 mL) at 0° C. under nitrogen was added methylhydrazine (0.36 mL, 6.82 mmol) and allowed to warm to room temperature. After stirring for two hours the reaction mixture was concentrated in vacuo and charged with diethylether. The solids were filtered off and the filtrate was collected and concentrated to afford O-(2,2-dimethyl-[1,3]dioxan-5-yl)-hydroxylamine as a yellow oil (0.97 g, 100%). 1H NMR (400 MHz; DMSO-d6) δ 5.98 (bs, 2H), 3.84-3.87 (m, 2H), 3.66-3.68 (m, 2H), 3.30-3.35 (m, 1H), 1.29 (s, 3H), 1.22 (s, 3H); MS (APCI+)=147.9.

Workup

  1. concentrationwas concentrated in vacuo
  2. additioncharged with diethylether
  3. filtrationThe solids were filtered off
  4. customthe filtrate was collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6059abd0841a46d4a5e7371949408e11
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

Loading…