Hydrochloric Acid → HCID 86622731, compound

HRID 2410344Notes

Reaction equation

HRID 2410344 reaction equation
[OH-:1].[Na+].[F:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:5]=1[CH:6]=O.Cl.[NH2:18]O.Cl>C(O)C.O>[F:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:5]=1[CH:6]=[N:18][OH:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86622730HCID 86622730, compound

Product 1

HCID 86622731HCID 86622731, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

50% aq. Sodium hydroxide (1.2 mL, 15.0 mmol) was added to a mixture of 2-fluoro-6-isobutoxybenzaldehyde (1.2 g, 6.1 mmol, EXAMPLE 16, Step 2) and hydroxylamine hydrochloride (0.47 g, 6.7 mmol) in ethanol (24 mL) and water (48 mL) at 0° C. The mixture was warmed to room temperature and stirred for 3 h. The mixture was neutrized with 2N hydrochloric acid and extracted with dichloromethane (100 mL×2). The combined extracts were dried over magnesium sulfate and concentrated in vacuo to give a solid. The residual solid was purified by silica gel column chromatography (hexane/ethyl acetate 9:1 to 6:1) to give 0.99 g (77%) of the title compound as a white solid.

Workup

  1. extractionextracted with dichloromethane (100 mL×2)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a solid
  5. customThe residual solid was purified by silica gel column chromatography (hexane/ethyl acetate 9:1 to 6:1)

Sources & evidence

ORD record
ord-46f7428f0a444dc1a727c49831eae186
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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