Hydroxylamine → HCID 136251062, compound

HRID 1864736Notes

Reaction equation

HRID 1864736 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:18][CH:19]=2)[N:14]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C:13]=1[CH3:36])=O.Cl.[NH2:38][OH:39].NO>N1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:18][CH:19]=2)[N:14]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C:13]=1[CH3:36])=[N:38][OH:39]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 443297Hydroxyamine hydrochlorideHCID 18438954HCID 18438954, compound

Product 1

HCID 136251062HCID 136251062, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 8 (16 mmol), hydroxylamine hydrochloride (10 eq, 11.2 g) and pyridine (270 mL) was heated to 80° C. for 24 hours. Additional hydroxylamine (3 g) was added and the temperature was increased to 90° C. After LC analysis confirmed the consumption of starting material, the reaction was cooled and the pyridine removed by rotary evaporation. The residue was dissolved in DCM and washed with water and 1M HCl. The organic layer was dried over Na2SO4 and concentrated. The reaction mixture was purified by flash chromatography eluting with 20% EtOAc/hexanes, Rf=0.4. The product was isolated as a white foam.

Workup

  1. customthe consumption of starting material
  2. temperaturethe reaction was cooled
  3. customthe pyridine removed by rotary evaporation
  4. dissolutionThe residue was dissolved in DCM
  5. washwashed with water and 1M HCl
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe reaction mixture was purified by flash chromatography
  9. washeluting with 20% EtOAc/hexanes, Rf=0.4
  10. customThe product was isolated as a white foam

Sources & evidence

ORD record
ord-dce2f5d0c59a4cb28d3235d54305b9f4
Source dataset
uspto-grants-2009_12
Patent number
US07625933B2

Reaction notes

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