Hydroxylamine → HCID 21104750, compound

HRID 1354185Notes

Reaction equation

HRID 1354185 reaction equation
[C:1]1([CH:7]([C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=2)C(=O)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19]O.[CH:21](O)([CH3:23])C>>[C:5]1([CH2:6][C:1]2[CH:7]=[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[O:18][N:19]=2)[CH:4]=[CH:3][CH:2]=[CH:23][CH:21]=1

Participants

4

Reactant 3

HCID 787HydroxylamineHCID 3776IsopropanolHCID 69417194HCID 69417194, compound

Product 1

HCID 21104750HCID 21104750, compound

Procedure

A mixture of phenylnicotinoyl acetone 0.500 g (0.0021 mol), isopropyl alcohol (5 ml) and hydroxylamine free base (in 7 ml methanol) was stirred at room temperature for 3 days (72 hrs.). The reaction mixture was concentrated to dryness and purified by column chromatography using a mixture of ethylacetate and hexanes (3:1). The purified compound (oxime) was dissolved in IPA (10 ml) and to it was added 2 N HCl (4 drops). The reaction mixture was refluxed for 8 hrs. The reaction mixture is finally concentrated to dryness to yield the desired compound as a pale yellow solid:

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified by column chromatography
  3. additiona mixture of ethylacetate and hexanes (3:1)
  4. dissolutionThe purified compound (oxime) was dissolved in IPA (10 ml) and to it
  5. additionwas added 2 N HCl (4 drops)
  6. temperatureThe reaction mixture was refluxed for 8 hrs
  7. concentrationThe reaction mixture is finally concentrated to dryness

Sources & evidence

ORD record
ord-2fb3745e11c240eda4134883bf61c647
Source dataset
uspto-grants-2007_05
Patent number
US07223777B2

Reaction notes

Loading…