Hydroxyamine hydrochloride → HCID 71254945, compound

HRID 1508344Notes

Reaction equation

HRID 1508344 reaction equation
[Cl:1][C:2]1[C:3]([F:19])=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]([O:15]CC)=[O:14])[C:9]=2[CH3:18])[CH:5]=[CH:6][CH:7]=1.Cl.NO>CCO>[Cl:1][C:2]1[C:3]([F:19])=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]([OH:15])=[O:14])[C:9]=2[CH3:18])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 71254971HCID 71254971, compound

Product 1

HCID 71254945HCID 71254945, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 5-(3-chloro-2-fluorophenyl)-4-methylisoxazole-3-carboxylate: The mixture of Intermediate 47C (0.057 g, 0.199 mmol) and hydroxylamine hydrochloride (0.017 g, 0.239 mmol) in EtOH (1 mL) was heated in a sealed tube at 90° C. After 5 h, the reaction was cooled to rt and then it was concentrated. Purification by reverse phase HPLC afforded the desired product (0.022 g, 39%) as a white solid. MS(ESI) m/z: 284.0 (M+H)+. 1H NMR (500 MHz, MeOD) δ 7.73-7.68 (m, 1H), 7.56 (ddd, J=7.8, 6.2, 1.7 Hz, 1H), 7.37 (td, J=8.0, 1.1 Hz, 1H), 4.45 (q, J=7.0 Hz, 2H), 2.24 (d, J=2.2 Hz, 3H), 1.42 (t, J=7.2 Hz, 3H) ppm.

Workup

  1. temperaturethe reaction was cooled to rt
  2. concentrationit was concentrated
  3. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-211415ffac6e44a2a47551ba4c6e15ad
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

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