O-Methylhydroxylamine hydrochloride → HCID 76603711, compound

HRID 251956Notes

Reaction equation

HRID 251956 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH:12]=[CH:11][C:10]([CH:13]=O)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.[CH3:16][O:17][NH2:18]>N1C=CC=CC=1>[CH3:16][O:17][N:18]=[CH:13][C:10]1[CH:11]=[CH:12][N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 86087806HCID 86087806, compound

Product 1

HCID 76603711HCID 76603711, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.00 g of 1-(3-chloro-2-pyridinyl)-1H-pyrazole-3-carbaldehyde, 1.21 g of O-methylhydroxylamine hydrochloride and 8 ml of pyridine was heated to reflux for 1 hour. After the reaction mixture was concentrated under reduced pressure, an aqueous saturated sodium hydrogen carbonate solution was poured into the residue and the mixture was extracted with methyl t-butyl ether three times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 2.23 g of 1-(3-chloro-2-pyridinyl)-1H-pyrazole-3-carbaldehyde O-methyloxime of the formula:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure
  4. additionan aqueous saturated sodium hydrogen carbonate solution was poured into the residue
  5. extractionthe mixture was extracted with methyl t-butyl ether three times
  6. washwashed successively with water
  7. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6ae639807764e8fa533262602e8e4c6
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

Loading…