O-Methylhydroxylamine hydrochloride → (E)-1-(4-chlorophenyl)-N-methoxy-2-pyrazol-1-ylethanimine

HRID 423102Notes

Reaction equation

HRID 423102 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH2:13][N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)=[CH:8][CH:7]=1>>[CH3:3][O:2]/[N:4]=[C:12](\[C:9]1[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=1)/[CH2:13][N:14]1[CH:18]=[CH:17][CH:16]=[N:15]1

Participants

3

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 437980581-(4-Chlorophenyl)-2-(1H-pyrazol-1-yl)ethanone2×

Product 1

HCID 57750295(E)-1-(4-chlorophenyl)-N-methoxy-2-pyrazol-1-ylethanimineYield 87%

Procedure

Methoxylamine hydrochloride (0.668 g, 8.00 mmol), was added to a stirred solution of 1-(4-chlorophenyl)-2-(1H-pyrazol-1-yl)ethanone (Intermediate 90) (1.103 g, 5 mmol), at room temperature under argon. The resulting solution was stirred at room temperature overnight. The pyridine was evaporated in vacuo and the residual solid was triturated with a saturated aqueous solution of sodium hydrogencarbonate (50-100 ml). The solid was filtered, washed with water and dried to afford (Z) and (E)-1-(4-chlorophenyl)-2-(1H-pyrazol-1-yl)ethanone O-methyl oxime (1.080 g, 87%) as a dark yellow solid.

Workup

  1. customThe pyridine was evaporated in vacuo
  2. customthe residual solid was triturated with a saturated aqueous solution of sodium hydrogencarbonate (50-100 ml)
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ebedd792ca684876907ecc6c2f5e3cf8
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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