Hydroxyamine hydrochloride → HCID 68380288, compound

HRID 2178658Notes

Reaction equation

HRID 2178658 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:6].Cl.[NH2:19]O>C(O)C>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:5]1[O:6][N:19]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 27714734,4,4-trifluoro-1-(2-methoxyphenyl)butane-1,3-dione

Product 1

HCID 68380288HCID 68380288, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,4,4-trifluoro-1-(2-methoxyphenyl)butane-1,3-dione (C9) (933 mg, 3.79 mmol) and hydroxylamine hydrochloride (798 mg, 11.4 mmol) in ethanol (10 mL) was refluxed under nitrogen for 3 hours, then cooled to room temperature. The reaction was concentrated in vacuo, treated with water (30 mL) and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 20% ethyl acetate in heptanes) afforded the title compound as a yellow oil. Yield: 502 mg, 2.06 mmol, 54%. GCMS m/z 243 (M+). 1H NMR (400 MHz, CDCl3) δ 4.00 (s, 3H), 7.01 (s, 1H), 7.05 (dd, J=8.4, 0.9 Hz, 1H), 7.11 (ddd, J=7.8, 7.4, 1.1 Hz, 1H), 7.48 (ddd, J=8.4, 7.4, 1.8 Hz, 1H), 8.00 (dd, J=7.8, 1.7 Hz, 1H).

Workup

  1. temperaturewas refluxed under nitrogen for 3 hours
  2. concentrationThe reaction was concentrated in vacuo
  3. additiontreated with water (30 mL)
  4. extractionextracted with dichloromethane (3×10 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification via silica gel chromatography (Gradient: 0% to 20% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-989114dc178d4ee2a03e24e608bc508f
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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