Hydroxylamine → HCID 136351073, compound

HRID 1505279Notes

Reaction equation

HRID 1505279 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=[C:11]([CH:14]=O)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:20][OH:21]>CCO.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=[C:11]([CH:14]=[N:20][OH:21])[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 787Hydroxylamine2×HCID 58497942HCID 58497942, compound

Product 1

HCID 136351073HCID 136351073, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-carbaldehyde (2 g) in EtOH (4 mL) and H2O (2 drops), was added aqueous NH2OH (50% in water, 0.48 mL). The solution was stirred at room temperature for 3 hours then allowed to stand at room temperature for 16 hours. Then the solution was stirred again and more hydroxylamine (0.04 mL) was added. After 3 hours, the reaction was quenched by addition of water. After extraction with ethylacetate, the organic phase was separated, dried over magnesium sulfate and concentrated to give 2.02 g of a yellow solid which was used in the next step without further purification. 1H-NMR (CDCl3, 400 MHz) shows a mixture of diastereoisomers: 8.07 and 7.94 (s, 1H), 7.43-7.38 (m, 3H), 3.88 (d, 1H), 3.50 (d, 1H).

Workup

  1. waitto stand at room temperature for 16 hours
  2. stirringThen the solution was stirred again
  3. waitAfter 3 hours
  4. customthe reaction was quenched by addition of water
  5. extractionAfter extraction with ethylacetate
  6. customthe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a61339099df044529abbb2fd8525ac8c
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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