Pyrrolidine → HCID 88351709, compound

HRID 862106Notes

Reaction equation

HRID 862106 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([CH:17]=1)[C:7]([C:9]1[C:14]([C:15]#[N:16])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8].Cl.[C:20]([O:24][NH2:25])([CH3:23])([CH3:22])[CH3:21].N1CCCC1>C(O)CC>[C:20]([O:24]/[N:25]=[C:15](/[C:14]1[C:9]([C:7](=[O:8])[C:6]2[CH:17]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[OH:18])=[N:10][CH:11]=[CH:12][CH:13]=1)\[NH2:16])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 19701583HCID 19701583, compound

Product 1

HCID 88351709HCID 88351709, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 2-(5-chloro-2-hydroxybenzoyl)-3-cyanopyridine (217 mg), O-t-butylhydroxylamine hydrochloride (158 mg), pyrrolidine (149 mg) and n-propanol (4.0 ml) was heated for 30 minutes under reflux. The reaction mixture was poured into a saturated aqueous saline solution, which was subjected to extraction with ethyl acetate. The extract solution was washed successively with an aqueous solution of potassium hydrogensulfate and a saturated aqueous saline solution, dried (anhydrous sodium sulfate), and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to give (Z)-2-(5-chloro-2-hydroxybenzoyl)-3-carbamoylpyridine O-t-butyloxime (251 mg) (Compound 152).

Workup

  1. temperaturewas heated for 30 minutes
  2. temperatureunder reflux
  3. additionThe reaction mixture was poured into a saturated aqueous saline solution, which
  4. extractionwas subjected to extraction with ethyl acetate
  5. washThe extract solution was washed successively with an aqueous solution of potassium hydrogensulfate
  6. dry with materiala saturated aqueous saline solution, dried (anhydrous sodium sulfate)
  7. concentrationconcentrated
  8. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-599389b5ab534327ac718e17553a10cd
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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