Water → 1-(9,9-Di-n-butyl-7-nitrofluorene-2-yl)-ethanone oxime

HRID 630645Notes

Reaction equation

HRID 630645 reaction equation
[CH2:1]([C:5]1([CH2:24][CH2:25][CH2:26][CH3:27])[C:17]2[CH:16]=[C:15]([C:18](=O)[CH3:19])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([N+:21]([O-:23])=[O:22])=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH3:4].Cl.[NH2:29][OH:30].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:1]([C:5]1([CH2:24][CH2:25][CH2:26][CH3:27])[C:17]2[CH:16]=[C:15]([C:18](=[N:29][OH:30])[CH3:19])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([N+:21]([O-:23])=[O:22])=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 1179383241-(9,9-Di-n-butyl-7-nitrofluorene-2-yl)-ethanone

Product 1

HCID 1317354121-(9,9-Di-n-butyl-7-nitrofluorene-2-yl)-ethanone oximeYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After 5.0 g of 1-(9,9-di-n-butyl-7-nitrofluorene-2-yl)-ethanone (6) (13.7 mmol) was dispersed in 150 ml of ethanol and 1.04 g of hydroxylamine hydrochloride (15.1 mmol) and 1.24 g of sodium acetate (15.1 mmol) were added thereto, the reaction mixture was slowly heated and refluxed for 1 hour. The reaction mixture was cooled to room temperature and 100 ml of distilled water was added thereto. Then, a solid product obtained by stirring the reaction mixture for about 30 minutes was filtered and washed with distilled water several times, followed by drying, thereby obtaining 4.89 g of 1-(9,9-di-n-butyl-7-nitrofluorene-2-yl)-ethanone oxime (7) (93.9%) as a light yellow product.

Workup

  1. temperaturethe reaction mixture was slowly heated
  2. temperaturerefluxed for 1 hour
  3. customThen, a solid product obtained
  4. filtrationwas filtered
  5. washwashed with distilled water several times
  6. customby drying

Sources & evidence

ORD record
ord-2f2e1570ca2a4a7ebc4c583352fb1319
Source dataset
uspto-grants-2016_04
Patent number
US09316906B2

Reaction notes

Loading…