Nitric Acid → 8-Nitro-1,2,4,5-tetrahydro-benzo[c]azepin-3-one

HRID 1041764Notes

Reaction equation

HRID 1041764 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][C:3](=[O:12])[NH:2]1.[N+:13]([O-])([OH:15])=[O:14]>>[N+:13]([C:9]1[CH:10]=[CH:11][C:6]2[CH2:5][CH2:4][C:3](=[O:12])[NH:2][CH2:1][C:7]=2[CH:8]=1)([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 28330792,3,4,5-tetrahydro-1H-2-benzazepin-3-one

Product 1

HCID 672643588-Nitro-1,2,4,5-tetrahydro-benzo[c]azepin-3-one

Conditions

Temperature
25 °C

Procedure

At 0° C., 1,2,4,5-tetrahydro-benzo[c]azepin-3-one (1 g, 6.2 mmol) was added to fuming nitric acid (3 mL) and the mixture was slowly warmed up to 25° C. during 1 h. The mixture was stirred at ambient temperature for 1 h and poured onto ice. The mixture was extracted with dichloromethane (3×50 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The crude mixture was then recrystallized from dichloromethane/hexane to give 8-nitro-1,2,4,5-tetrahydro-benzo[c]azepin-3-one (0.2 g). 1H NMR (300 MHz, CDCl3) δ 8.12 (dd, 1H), 8.03 (d, 1H), 7.37 (d, 1H), 4.47 (d, 2H), 3.2 (m, 2H), 2.8 (m, 2H).

Workup

  1. additionpoured onto ice
  2. extractionThe mixture was extracted with dichloromethane (3×50 mL)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was then recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-dae3ebd080e24a4c9ccf455a5418a89d
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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