Hydroxyamine hydrochloride → HCID 86752926, compound

HRID 1957259Notes

Reaction equation

HRID 1957259 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH:19]=O)[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(=O)(O)[O-].[Na+].Cl.[NH2:27][OH:28]>O1CCCC1>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH:19]=[N:27][OH:28])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 186929322-Chloro-5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]benzaldehyde

Product 1

HCID 86752926HCID 86752926, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

22.6 g of 3-chloro-2-(4-chloro-3-formylphenyl)-5-trifluoromethylpyridine, 6.5 g of sodium bicarbonate and 5.4 g of hydroxylamine hydrochloride in 100 ml of tetrahydrofuran were stirred at 23° C. for 24 hours. The tetrahydrofuran was then removed, after which the residue was taken up in 100 ml of methylene chloride. The solution was washed twice with 100 ml of water. The solid formed during this was removed, washed with water and dried. Concentration of the organic phase resulted in a residue which was purified by chromatography on silica gel with cyclohexane/ethyl acetate (7:3). Yield: 26.1 g (82%) of colorless crystals; melting point: 173°-174° C.

Workup

  1. customThe tetrahydrofuran was then removed
  2. washThe solution was washed twice with 100 ml of water
  3. customThe solid formed during
  4. customthis was removed
  5. washwashed with water
  6. customdried
  7. customConcentration of the organic phase resulted in a residue which
  8. customwas purified by chromatography on silica gel with cyclohexane/ethyl acetate (7:3)

Sources & evidence

ORD record
ord-5ab8592f646b46b2be451895b282f07a
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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