Pyridine → HCID 136414661, compound

HRID 1921265Notes

Reaction equation

HRID 1921265 reaction equation
[C:1]12([C:11]([C:13]3[C:18]([OH:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=3[Cl:21])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl.[NH2:23][OH:24].N1C=CC=CC=1>CCOC(C)=O.C1(C)C=CC=CC=1>[C:1]12([C:11]([C:13]3[C:18]([OH:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=3[Cl:21])=[N:23][OH:24])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 23117157HCID 23117157, compound

Product 1

HCID 136414661HCID 136414661, compound

Reagents, catalysts & solvents 1

HCID 21584019Toluene ethylacetateSolvent

Procedure

1-adamantyl-(2-chloro-4,6-dihydroxyphenyl)methanone (1.9 g, 6.2 mmoles), hydroxylamine hydrochloride (100 g) and pyridine (50 ml) were refluxed for 4 h. The mixture was concentrated under vacuum, poured into water, extracted with ethyl acetate, washed with HCl 1N, dried over Na2SO4 and concentrated under vacuum to give the crude product. Flash chromatography (AcOEt/toluene 3/7) gave the pure oxime (1 g as a solid, 50%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionpoured into water
  3. extractionextracted with ethyl acetate
  4. washwashed with HCl 1N
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customto give the crude product

Sources & evidence

ORD record
ord-09fb0241a03d4e53ac77756d871ca0ea
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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