Isoamyl Nitrite → 1-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethane-1,2-dione 2-oxime

HRID 2172365Notes

Reaction equation

HRID 2172365 reaction equation
[CH2:1]([CH:3]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22](=[O:32])[C:23]3[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=3[CH3:31])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:33](=[O:41])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH:10]=2)[CH3:2].[N:46](OCCC(C)C)=[O:47]>C1COCC1>[CH2:1]([CH:3]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22](=[O:32])[C:23]3[C:24]([CH3:31])=[CH:25][C:26]([CH3:30])=[CH:27][C:28]=3[CH3:29])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:33](=[O:41])[C:34]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[N:46][OH:47])[CH:10]=2)[CH3:2]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 866905311-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethanone

Product 1

HCID 866905321-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethane-1,2-dione 2-oximeYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 1-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethanone (1.20 g, 2.03 mmol) and isoamyl nitrite (0.50 g, 4.26 mmol) in THF (6 ml) is bubbled with HCl gas for 1 minute. After stirring at room temperature for 4 hours, the reaction mixture is poured into ice-water. The crude product is extracted with CH2Cl2, and washed with water and brine. After drying over MgSO4 and concentration, the crude is purified by column chromatography on silica gel eluting with a mixed solvent of n-hexane and CH2Cl2 (1:1) to obtain an off-white resin (0.69 g, 50%). The structure is confirmed by 1H-NMR spectrum (CDCl3) δ [ppm]: 0.79-0.90 (m), 1.19-1.45 (m), 2.19 (s), 2.28 (m), 2.42 (s), 4.75 (m), 6.97 (s), 7.35-7.41 (m), 7.57 (d), 7.63 (d), 7.70-7.79 (m), 7.98 (d), 8.35 (s), 8.63 (d), 8.72 (s), 9.54 (d).

Workup

  1. customis bubbled with HCl gas for 1 minute
  2. additionthe reaction mixture is poured into ice-water
  3. extractionThe crude product is extracted with CH2Cl2
  4. washwashed with water and brine
  5. dry with materialAfter drying over MgSO4 and concentration
  6. customthe crude is purified by column chromatography on silica gel eluting with a mixed solvent of n-hexane and CH2Cl2 (1:1)

Sources & evidence

ORD record
ord-dcd9d12a2aba455d919bcc2d1fc12df9
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

Loading…