Hydroxyamine hydrochloride → HCID 136413191, compound

HRID 1502383Notes

Reaction equation

HRID 1502383 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH3:9])[C:5]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[CH3:20])=[CH:4][N:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:27][OH:28]>C(O)C.ClC(Cl)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[N:27][OH:28])[CH3:9])[C:5]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[CH3:20])=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86674957HCID 86674957, compound

Product 1

HCID 136413191HCID 136413191, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(2-chloro-5-((5-fluoro-2-methylphenyl)ethynyl)pyridin-4-yl)ethanone (700 mg, 2.0 mmol), sodium acetate (320 mg, 3.9 mmol), and hyroxylamine hydrochloride (254 mg, 3.65 mmol) in ethanol (11 mL) and dichloroethane (1.6 mL) was heated at 70° C. for 15 minutes. The cooled reaction mixture was evaporated in vacuo to afford a residue that was redissolved in ethyl acetate (150 mL) and washed with water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a white solid that was used in the next step without further purification.

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated in vacuo
  3. customto afford a residue that
  4. washwashed with water (100 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto afford a white solid that
  10. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-c9669938aaab41f6a241cbd71e22984c
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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