Hydroxyamine hydrochloride → HCID 136331255, compound

HRID 875203Notes

Reaction equation

HRID 875203 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.Cl.[NH2:16][OH:17]>N1C=CC=CC=1>[OH:17][N:16]=[C:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 12325240(1-Methyl-1H-imidazol-2-yl)(phenyl)methanone

Product 1

HCID 136331255HCID 136331255, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (1-methyl-1H-imidazol-2-yl)(phenyl)methanone (20.8 g, 112 mmol) and hydroxylamine hydrochloride (19.4 g, 279 mmol) in pyridine (120 mL) was stirred 8 h at 50° C. then overnight at room temperature. After removal of the solvent in vacuo, addition of water (500 mL) induced precipitation of a white solid that was filtered off, washed with water (2×50 mL) and dried. A second filtration of the liquor yielded a second crop of solid. The combined crops afforded N-hydroxy-1-(1-methyl-1H-imidazol-2-yl)-1-phenylmethanimine [18.5 g, yield 80%; HPLC/MS: m/z=202 (M+H); log P(HCOOH)=0.24].

Workup

  1. customovernight
  2. customat room temperature
  3. customAfter removal of the solvent
  4. additionin vacuo, addition of water (500 mL)
  5. customprecipitation of a white solid
  6. filtrationthat was filtered off
  7. washwashed with water (2×50 mL)
  8. customdried
  9. filtrationA second filtration of the liquor
  10. customyielded a second crop of solid

Sources & evidence

ORD record
ord-ff1061ca5fb64c7fa824f5a27da3441a
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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