Ammonia → Methyl N-hydroxy-2-phenylethanimidate

HRID 1252549Notes

Reaction equation

HRID 1252549 reaction equation
Cl.[C:2]1([CH2:8][C:9](=[NH:12])[O:10][CH3:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N[OH:15].N>CN(C)C=O>[OH:15][N:12]=[C:9]([O:10][CH3:11])[CH2:8][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 443297Hydroxyamine hydrochlorideHCID 12433430Methyl 2-phenylethanimidate--hydrogen chloride (1/1)

Product 1

HCID 71372123Methyl N-hydroxy-2-phenylethanimidateYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl phenylacetimidate hydrochloride (30.9 grams; 0.167 mole) was stirred with solid hydroxylamine hydrochloride (12.8 grams; 0.184 mole) in dimethyl formamide (120 ml) while ammonia gas was added slowly without cooling. Ammonia addition (approximately 5 grams) was stopped when the temperature of the mixture peaked at 40° C. and dropped to 29° C. The slurry was then cooled in an ice bath and filtered. The filtrate (131 grams) was analyzed by GC and GC-mass spectroscopy and established to contain methyl N-hydroxyphenylacetimidate (23.4 grams; 84.8% yield).

Workup

  1. additionwas added slowly
  2. temperaturewithout cooling
  3. custompeaked at 40° C.
  4. additiondropped to 29° C
  5. temperatureThe slurry was then cooled in an ice bath
  6. filtrationfiltered

Sources & evidence

ORD record
ord-9e799d12c54a44ada6c6344c505327ff
Source dataset
uspto-grants-1988_05
Patent number
US04743701

Reaction notes

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