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

HRID 1922393Notes

Reaction equation

HRID 1922393 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[N-:12]=[N+]=[N-].[Na+].OS(O)(=O)=O>C(Cl)(Cl)Cl.O>[NH:12]1[C:1](=[O:11])[CH2:2][CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]1=2

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 107241-TetraloneHCID 33557Sodium Azide

Product 1

HCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-oneYield 65.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 3,4-dihydronaphthalen-1(2H)-one (2.0 g, 13.68 mmol) and sodium azide (1.11 g, 17.10 mmol) in a mixture of 14 mL CHCl3 and 3 mL H2O was heated at 40° C. then treated with H2SO4 dropwise over 20 minutes. The mixture was diluted with 50 mL H2O and filtered. The solid was slurried in hot H2O, cooled and filtered to give a gray solid (1.45 g, 65.6%). 1H-NMR (DMSO-d6) δ 9.49 (s, 1H), 7.25-7.22 (m, 2H), 7.19-7.21 (m, 1H), 6.95 (d, J=7.8 Hz, 1H), 2.70-2.65 (m, 2H), 2.15-2.07 (m, 4H). MS (EI): 161 (M+).

Workup

  1. filtrationfiltered
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-3229eb66c0d54011a0fa849147195357
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…