Hydroxyamine hydrochloride → HCID 136333673, compound

HRID 1057824Notes

Reaction equation

HRID 1057824 reaction equation
[OH:1][C:2]1[C:16]([CH2:17][CH2:18][CH3:19])=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=O)=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22]>N1C=CC=CC=1>[OH:1][C:2]1[C:16]([CH2:17][CH2:18][CH3:19])=[CH:15][C:5]([C:6](=[N:21][OH:22])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 18672472HCID 18672472, compound

Product 1

HCID 136333673HCID 136333673, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-hydroxy-5-propyl-2′-fluorobenzophenone (Step A; 1.35 g, 5.23 mmol) in 15 mL of pyridine was treated with hydroxylamine hydrochloride (1.82 g, 26.15 mmol). The mixture was refluxed for 24 hours, cooled and the pyridine removed in vacuo. The residue was taken up in ethyl acetate and washed with 1N hydrochloric acid, water, brine, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified via flash chromatography on silica gel (20% ethyl acetate/hexane eluent) to yield the title compound.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. temperaturecooled
  3. customthe pyridine removed in vacuo
  4. washwashed with 1N hydrochloric acid, water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified via flash chromatography on silica gel (20% ethyl acetate/hexane eluent)

Sources & evidence

ORD record
ord-f9250c082d0a4f54a1e67bdd559a3356
Source dataset
uspto-grants-2003_02
Patent number
US06515015B1

Reaction notes

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