Nitric Acid → 7-nitro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

HRID 1922394Notes

Reaction equation

HRID 1922394 reaction equation
[NH:1]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[N+:13]([C:10]1[CH:11]=[CH:12][C:2]2[NH:1][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=2[CH:9]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 3561757-nitro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (1.42 g, 8.81 mmol) in conc. H2SO4 (25 mL) was treated with fuming HNO3 (414 μL, 8.81 mmol) at −5 to −10° C. (ice/MeOH). The resulting solution was stirred at the same temperature for 30 minutes. The reaction was quenched with the addition of crushed ice. The resulting suspension was diluted with H2O (50 mL) and filtered. The solid was washed with 4×50 mL H2O, collected and dried under reduced pressure overnight. Yield: 1.0 g, 55.1%. 1H-NMR (DMSO-d6) δ 10.08 (s, 1H), 8.19 (d, J=2.4 Hz, 1H), 8.11 (dd, J=2.4, 8.7 Hz, 1H), 7.15 (d, J=8.7 Hz, 1H), 2.83-2.79 (m, 2H), 2.26-2.13 (m, 4H). MS (EI): 206 (M+).

Workup

  1. customThe reaction was quenched with the addition of crushed ice
  2. additionThe resulting suspension was diluted with H2O (50 mL)
  3. filtrationfiltered
  4. washThe solid was washed with 4×50 mL H2O
  5. customcollected
  6. customdried under reduced pressure overnight

Sources & evidence

ORD record
ord-da96b728c2104b8ea7c3d8248a252def
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…