Water → 2-(4-Dimethoxymethyl-2-methoxy-3-nitrophenoxy)ethylamine

HRID 1821436Notes

Reaction equation

HRID 1821436 reaction equation
[CH3:1][O:2][CH:3]([O:29][CH3:30])[C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10]C23C=CC=CC2C(NC3=O)=O)=[C:6]([O:24][CH3:25])[C:5]=1[N+:26]([O-:28])=[O:27].O.[NH2:32]N.O>C(O)C>[CH3:1][O:2][CH:3]([O:29][CH3:30])[C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][NH2:32])=[C:6]([O:24][CH3:25])[C:5]=1[N+:26]([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 866282232-[2-(4-Dimethoxymethyl-2-methoxy-3-nitrophenoxy)ethyl]phtalimide

Product 1

HCID 689994632-(4-Dimethoxymethyl-2-methoxy-3-nitrophenoxy)ethylamineYield 116.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[2-(4-dimethoxymethyl-2-methoxy-3-nitrophenoxy)ethyl]phtalimide (0.05 g, 0.12 mmol) obtained in Step 2 in ethanol (1.0 mL) was added with hydrazine monohydrate (6.4 μL, 0.13 mmol) and heated under reflux for 3 hours. The reaction mixture was cooled to room temperature and added with water, followed by extracting with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain 2-(4-dimethoxymethyl-2-methoxy-3-nitrophenoxy)ethylamine (0.04 g, 100%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. extractionby extracting with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d2b8d37206694ab4b14e60d9a32a8f4f
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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