1-Tetralone → 1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

HRID 1292904Notes

Reaction equation

HRID 1292904 reaction equation
[N-:1]=[N+]=[N-].[Na+].[C:5]1(=[O:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[OH-].[Na+]>CS(O)(=O)=O>[NH:1]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6][C:5]1=[O:15]

Participants

5

Reactant 3

HCID 107241-TetraloneHCID 14798Sodium HydroxideHCID 33557Sodium Azide

Product 1

HCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-oneYield 85%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
0 °C

Procedure

Sodium azide (1.95 g, 30 mmol) was added in small portions to a solution of 3,4-dihydro-1(2H)-naphthalenone (2.92 g, 20 mmol) in CH3SO3H (50 mL) at 0° C. The mixture was stirred at 0° C. for 15 min, hr at room temperature, poured into ice (400 mL), basified until pH>8 with 1N NaOH at 0° C. and extracted with ether (3×100 mL). The combined organic layer was dried (MgSO4), concentrated in vacuo and flash column chromatography (EtOAc:hexane/1:1) gave 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (2.71 g, 85%) as a white solid. 1H NMR (CDCl3, 300 MHz) δ2.18-2.32 (m, 2H), 2.36 (t, J=7.1 Hz, 2H), 2.80 (t, J=7.6 Hz, 2H), 6.99 (d, J=8.1 Hz, 1H), 7.13 (td, J=7.6, 1.5 Hz, 1H), 7.22 (d, J=7.0 Hz, 2H), 8.10 (br, 1H) ppm.

Workup

  1. extractionextracted with ether (3×100 mL)
  2. dry with materialThe combined organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo and flash column chromatography (EtOAc:hexane/1:1)

Sources & evidence

ORD record
ord-3cdf77b1fd0e4310be720a9574ccdbc3
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

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