Acetyl chloride → 1-(8-Nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-ethanone

HRID 74059

Reaction equation

HRID 74059 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[N+:5]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:12]=2[CH:18]=1)([O-:7])=[O:6].C([O-])(O)=O.[Na+]>C(Cl)Cl>[N+:5]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH2:16][CH2:15][CH2:14][N:13]([C:1](=[O:3])[CH3:2])[C:12]=2[CH:18]=1)([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 468640718-Nitro-2,3,4,5-tetrahydro-1H-1-benzazepine

Product 1

HCID 574702571-(8-Nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-ethanoneYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (1 g, 13 mmol) was added dropwise to a mixture of 8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.3 g, 6.8 mmol) and NaHCO3 (1 g, 12 mmol) in CH2Cl2 (50 mL). After stirring for 1 h, the mixture was filtered and the filtrate was concentrated. The residue was dissolved in CH2Cl2, washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography to give 1-(8-nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-ethanone as a yellow solid (1.3 g, 80%).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e79462d8cd284e94a03a0ee101e4eb14
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Linked notes

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