Potassium Carbonate → 1-(3-Amino-4-hydroxyphenyl)ethanone O-methyloxime

HRID 2070111Notes

Reaction equation

HRID 2070111 reaction equation
Cl.[CH3:2][O:3][NH2:4].[NH2:5][C:6]1[CH:11]=[C:10]([C:12]2([CH3:17])OCCO2)[CH:9]=[CH:8][C:7]=1[OH:18].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:2][O:3][N:4]=[C:12]([C:10]1[CH:9]=[CH:8][C:7]([OH:18])=[C:6]([NH2:5])[CH:11]=1)[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 59444173HCID 59444173, compound

Product 1

HCID 1363371921-(3-Amino-4-hydroxyphenyl)ethanone O-methyloxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of O-methylhydroxylamine hydrochloride (535 mg, 6.40 mmol), 2-amino-4-(2-methyl-1,3-dioxolan-2-yl)phenol D62 (250 mg, 1.28 mmol) and potassium carbonate (442 mg, 3.20 mmol) in ethanol (10 mL) was heated to reflux for 2 hr. The mixture was cooled to rt and concentrated to dryness under vacuum and the residue partitioned between DCM and water. The organic phase was separated washed with brine, dried (MgSO4) and concentrated to dryness in vacuo. The residue was purified using silica gel chromatography eluting with 0 to 10% MeOH in DCM. The title product was isolated as a pale brown solid, 224 mg, 97%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hr
  3. concentrationconcentrated to dryness under vacuum
  4. customthe residue partitioned between DCM and water
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated to dryness in vacuo
  9. customThe residue was purified
  10. washeluting with 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-fd8e231b555942fa91b02c35ed4a799d
Source dataset
uspto-grants-2012_10
Patent number
US08299257B2

Reaction notes

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