Pyrrolidine → HCID 136463775, compound

HRID 862102Notes

Reaction equation

HRID 862102 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[C:7]([C:9]1[C:14]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[CH:13][CH:12]=[CH:11][N:10]=1)=O.Cl.[C:23]([O:27][NH2:28])([CH3:26])([CH3:25])[CH3:24].N1CCCC1>C(O)CC>[C:23]([O:27]/[N:28]=[C:7](\[C:9]1[C:14]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[CH:13][CH:12]=[CH:11][N:10]=1)/[C:6]1[CH:20]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[OH:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 197016352-(5-Bromo-2-hydroxybenzoyl)-3-(1,3-dioxolan-2-yl)pyridine

Product 1

HCID 136463775HCID 136463775, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 2-(5-bromo-2-hydroxybenzoyl)-3-(1,3-dioxolan-2-yl)pyridine (2.92 g), O-t-butyl-hydroxylamine hydrochloride (2.09 g) and pyrrolidine (1.78 g) in n-propanol (40 ml) was heated for 2 hours under reflux. The reaction mixture was concentrated, to which was added water, followed by subjecting the mixture to extraction with ethyl acetate. The extract solution was washed with 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-bromo-2-hydroxybenzoyl)-3-(1,3-dioxolan-2-yl)pyridine O-t-butyloxime (2.81 g) (Compound 134).

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated, to which
  3. additionwas added water
  4. extractionto extraction with ethyl acetate
  5. washThe extract solution was washed with a saturated aqueous saline solution
  6. dry with materialdried (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-a0acd65784ad4ce680a9cb519443478b
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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