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

HRID 1835650Notes

Reaction equation

HRID 1835650 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 the product of Example 13, Step A, 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 2 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-47f0e6af8a0c45edb9aa41879ae2d214
Source dataset
uspto-grants-2004_08
Patent number
US06770778B2

Reaction notes

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