Hydrochloric Acid → HCID 178439643, compound

HRID 2289130Notes

Reaction equation

HRID 2289130 reaction equation
[CH:1]1([C:4]([C:6]2[CH:12]=[CH:11][C:9]([OH:10])=[C:8]([CH2:13][CH2:14][CH3:15])[C:7]=2[OH:16])=O)[CH2:3]C1.[NH2:17][OH:18].Cl.C([O-])(=O)C.[Na+]>CO.O>[CH:4]1([CH:6]2[C:12](=[N:17][OH:18])[CH:11]=[C:9]([OH:10])[C:8]([CH2:13][CH2:14][CH3:15])=[C:7]2[OH:16])[CH2:1][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 517045Sodium AcetateHCID 18701986HCID 18701986, compound

Product 1

HCID 178439643HCID 178439643, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-cyclopropylcarbonyl-2-(n-propyl)resorcinol (1.0 g, 4.54 mmole) in methanol (10 mL) was treated with hydroxylamine.HCl (1.58g, 22.7 mmole) and sodium acetate (1.86g, 22.7 mmole) and the mixture refluxed for 7 hours. The cooled mixture was poured into water and extracted 3× with ethyl acetate. The combined extracts were washed with water (2×), 10% sodium bicarbonate, brine, dried over magnesium sulfate and concentrated in vacuo to give a solid. The crude product was chromatographed on silica gel eluting with methylene chloride followed by methanol:methylene chloride (5:95) to afford the title compound. NMR (CDCl3); δ 0.89 (m, 2H); 0.94 (t, 3H); 1.10 (m, 2H); 1.76 (m, 1H); 2.61 (t, 2H); 6.35 (d, 1H); 7.41 (d, 1H).

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washThe combined extracts were washed with water (2×), 10% sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a solid
  6. customThe crude product was chromatographed on silica gel eluting with methylene chloride

Sources & evidence

ORD record
ord-8a3030a1c43c4084a5d6a194ff09e4d6
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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