Hydroxylamine → HCID 136251062, compound

HRID 1393334Notes

Reaction equation

HRID 1393334 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 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 eluding 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. customThe product was isolated as a white foam

Sources & evidence

ORD record
ord-021c294a7a6c454ebb357669bb2bd104
Source dataset
uspto-grants-2008_03
Patent number
US07345085B2

Reaction notes

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