Iodoethane → 3-Ethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1040596Notes

Reaction equation

HRID 1040596 reaction equation
[N+]([O-])(O)=O.[N+:5]([C:8]1[CH:18]=[CH:17][C:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:10]=2[CH:9]=1)([O-:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].I[CH2:26][CH3:27]>CC(C)=O>[CH2:26]([N:14]1[CH2:15][CH2:16][C:10]2[CH:9]=[C:8]([N+:5]([O-:7])=[O:6])[CH:18]=[CH:17][C:11]=2[CH2:12][CH2:13]1)[CH3:27]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 85577068HCID 85577068, compound

Product 1

HCID 189435263-Ethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7-Nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine nitrate salt (1.03 g/4 mmol) was suspended in acetone (10 mL). Potassium carbonate and iodoethane were added sequentially and the suspension was heated to reflux with vigorous stirring for 2 hours. The mixture was then filtered through a pad of celite (rinsing with acetone) and the filtrate concentrated onto silica gel. 3-Ethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine was isolated by column chromatography on silica gel (eluting with 0→10% methanol/methylene chloride) as a yellow/orange oil (600 mg/72%). 1H NMR (400 MHz, CDCl3) δ 7.98 (m, 2H), 7.28 (m, 1H), 3.15 (s, 4H), 2.91 (s, 4H), 2.79 (q, J=7.1 Hz, 2H), 1.20 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux
  3. filtrationThe mixture was then filtered through a pad of celite (rinsing with acetone)
  4. concentrationthe filtrate concentrated onto silica gel

Sources & evidence

ORD record
ord-d50c4c818b994988939a6facebfae050
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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