Hydroxyamine hydrochloride → HCID 86745179, compound

HRID 2371694Notes

Reaction equation

HRID 2371694 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=O.[ClH:16].[NH2:17][OH:18]>N1C=CC=CC=1>[ClH:16].[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[N:17][OH:18]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 15008262HCID 15008262, compound

Product 1

HCID 86745179HCID 86745179, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (4-amino-3-pyridinyl)cyclohexylmethanone (5 g) and hydroxylamine hydrochloride (10 g) in 70 ml pyridine was stirred at 80° C. for three hours and thereafter concentrated. The residue was stirred with water, basified with sodium carbonate and extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride solution. The dried (anhy. MgSO4) organic layer was concentrated to 9 g waxy solid. This solid was triturated with acetonitrile to yield 4.9 g solid, m.p. 155°-158° C. Three grams were converted to the hydrochloride salt in methanol/ether to yield 2.8 g solid, m.p. 226°-228° C.

Workup

  1. concentrationconcentrated
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water and saturated sodium chloride solution
  5. customThe dried (anhy
  6. concentrationMgSO4) organic layer was concentrated to 9 g waxy solid
  7. customThis solid was triturated with acetonitrile

Sources & evidence

ORD record
ord-0b92833604514f5da01fd00047ea4955
Source dataset
uspto-grants-1992_03
Patent number
US05095019

Reaction notes

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