Hydroxyamine hydrochloride → HCID 86711958, compound

HRID 1475267Notes

Reaction equation

HRID 1475267 reaction equation
O=[C:2]([CH2:7][C:8](=[O:20])[C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)[C:3]([O:5][CH3:6])=[O:4].[NH2:21]O.Cl>CO>[F:17][C:16]([F:19])([F:18])[O:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]2[O:20][N:21]=[C:2]([C:3]([O:5][CH3:6])=[O:4])[CH:7]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86711957HCID 86711957, compound

Product 1

HCID 86711958HCID 86711958, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2,4-dioxo-4-(4-(trifluoromethoxy)phenyl)butanoate (6.85 g, 23.6 mmol) and NH2OH.HCl (4.92 g, 70.8 mmol) in MeOH (120 mL) was refluxed for 4 h. The volatiles were removed under reduced pressure, the residue was taken up in CHCl3 (200 mL) and washed with H2O (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (6.50 g, 95.6%), which was used in the next step without further purification. MS (ES+) C12H8F3NO4 requires: 287. found: 288 [M+H]+.

Workup

  1. temperaturewas refluxed for 4 h
  2. customThe volatiles were removed under reduced pressure
  3. washwashed with H2O (50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a036226bf7a4cd095771dc75b670135
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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