Hydroxyamine hydrochloride → HCID 86650744, compound

HRID 875208Notes

Reaction equation

HRID 875208 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)=[CH:5][N:4]=[CH:3]1.Cl.[NH2:16][OH:17]>N1C=CC=CC=1>[OH:17][N:16]=[C:7]([C:6]1[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 914663HCID 914663, compound

Product 1

HCID 86650744HCID 86650744, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (1-methyl-1H-imidazol-5-yl)(phenyl)methanone (14.0 g, 75 mmol) and hydroxylamine hydrochloride (13.1 g, 188 mmol) in pyridine (60 mL) was stirred for 72 h at room temperature, and for 3 h at 50° C. After removal of the solvent in vacuo, addition of water (600 mL) and extraction with ethyl acetate (4×150 mL), the combined organic layers were washed with water (150 mL), dried over MgSO4 and concentrated in vacuo. The resulting yellow solid was washed with pentane to afford N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-phenylmethanimine [7.12 g, yield 42%; HPLC/MS: m/z=202 (M+H); log P(HCOOH)=0.41]. Further extraction of the neutralised combined aqueous layers afforded a second crop of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-phenylmethanimine [5.75 g, yield 34%; HPLC/MS: m/z=202 (M+H); log P(HCOOH)=0.41], combined yield 76%.

Workup

  1. customAfter removal of the solvent
  2. additionin vacuo, addition of water (600 mL) and extraction with ethyl acetate (4×150 mL)
  3. washthe combined organic layers were washed with water (150 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washThe resulting yellow solid was washed with pentane

Sources & evidence

ORD record
ord-4adb366300674ed7bd69bf39a0a39780
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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