Hydroxyamine hydrochloride → HCID 85862825, compound

HRID 2251472Notes

Reaction equation

HRID 2251472 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[CH3:7][O:8][CH:9]([O:18][CH3:19])[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1>CO>[CH3:7][O:8][CH:9]([O:18][CH3:19])[C:10]1[CH:17]=[CH:16][C:13]([C:14](=[N:2][OH:3])[NH2:15])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 135945214-(Dimethoxymethyl)benzonitrile

Product 1

HCID 85862825HCID 85862825, compoundYield 931.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of hydroxylamine hydrochloride (31.62 g; 45.5 mmol) in MeOH (350 ml) was treated with sodium methoxide (24.58 g; 45.5 mmol) slowly, in small portions. After stirring for 20 minutes, a solution of 4-(dimethoxymethyl)benzonitrile (67 g; 37.9 mmol) in MeOH (100 ml) was added and the mixture heated to reflux. After 12 hr, it was concentrated and partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated to afford 4-(dimethoxymethyl)-N′-hydroxybenzenecarboximidamide (74.2 g) which was used in the next step without further purification. MS: m/z 211 (M+1).

Workup

  1. temperaturethe mixture heated to reflux
  2. waitAfter 12 hr
  3. concentrationit was concentrated
  4. custompartitioned between ethyl acetate and water
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-467d1f5af428465ba8b83abb843cf136
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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