Water → 1-(5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)ethanone

HRID 470086Notes

Reaction equation

HRID 470086 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1([CH3:20])[CH2:12][CH2:11][CH2:10][NH:9][C:8]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:7]1=2.C([O-])(O)=O.[Na+].O>C(Cl)Cl>[CH3:5][C:6]1([CH3:20])[CH2:12][CH2:11][CH2:10][N:9]([C:1](=[O:3])[CH3:2])[C:8]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:7]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 574702565,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine

Product 1

HCID 578647131-(5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)ethanoneYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.77 mL, 11 mmol) was added to a suspension of crude 5,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.2 g, 5.45 mmol) and NaHCO3 (1.37 g, 16.3 mmol) in CH2Cl2 (20 mL). The mixture was heated at reflux for 1 h. After cooling, the mixture was poured into water and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography to afford 1-(5,5-dimethyl-8-nitro-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)ethanone (1.05 g, 64% over two steps).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureAfter cooling
  4. extractionextracted with CH2Cl2
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8e7baf5881a448ce98e459a5ecc68443
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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