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

HRID 2189674Notes

Reaction equation

HRID 2189674 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-70810025efed445bb850fe618767712f
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

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