Hydroxyamine hydrochloride → HCID 73509154, compound

HRID 1590246Notes

Reaction equation

HRID 1590246 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[C:11](O)=[C:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9]1.Cl.[NH2:23][OH:24]>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[C:11](=[N:23][OH:24])[CH:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 54691692HCID 54691692, compound

Product 1

HCID 73509154HCID 73509154, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the title compound of Example H (3.16 g, 10.8 mmol) in pyridine (50 ml) was added hydroxylamine hydrochloride (3.73 g, 54 mmol) and the reaction was stirred for 5 days(d) at room temperature. After the reaction was concentrated in vacuo, H2O was added and the mixture was extracted with CH2Cl2. Drying of the organic phase (MgSO4) and concentration gave a solid which was chromatographed on silica gel eluting with 2% EtOH/CH2Cl2 to give the title compound (1.91 g, 57%). Anal calcd for C15H17N2O4F: C, 58.44; H, 5.56; N, 9.09. Found: C, 58.43; H, 5.62; N, 8.75. DSC=175.1°-180.2° C. at 225.6 J/g.

Workup

  1. concentrationAfter the reaction was concentrated in vacuo, H2O
  2. additionwas added
  3. extractionthe mixture was extracted with CH2Cl2
  4. dry with materialDrying of the organic phase (MgSO4) and concentration
  5. customgave a solid which
  6. customwas chromatographed on silica gel eluting with 2% EtOH/CH2Cl2

Sources & evidence

ORD record
ord-b406934aaabf492286c1c8a73c9d945c
Source dataset
uspto-grants-1993_04
Patent number
US05202344

Reaction notes

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