Nitric Acid → 5,5-Dimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

HRID 1687171Notes

Reaction equation

HRID 1687171 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][C:6](=[O:9])[NH:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1=2.[N+:15]([O-])([OH:17])=[O:16].S(=O)(=O)(O)O.[OH-].[Na+].C(=O)(O)[O-].[Na+]>>[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][C:6](=[O:9])[NH:5][C:4]2[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][C:3]1=2

Participants

6

Reactant 5

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 570064745,5-Dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Product 1

HCID 578538385,5-Dimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Conditions

Temperature
0 °C

Procedure

5,5-Dimethyl-1,3,4,5-tetrahydrobenzo[b]azepin-2-one (514 mg, 2.716 mmol), WO 2005066165, was added to a 0° C. solution of 5 mL nitric acid and 5 mL sulfuric acid. The solution was stirred for 10 minutes at 0° C. ° C. The reaction was poured into a dilute NaOH/ice mixture. NaOH and sodium bicarbonate were added until the solution pH was neutral. A white precipitate formed, which was filtered off, washed with water and dried (485 mg, 76%) to yield 5,5-Dimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one. mp 208° C.; LCMS: m/z=235.03 (M+H+), 1H NMR (400 MHz, CDCl3) δ 8.38 (s, 1H), 8.35 (s, 1H), 8.10 (d, 1H, J=8.9 Hz), 7.06 (d, 1H, J=8.6 Hz), 2.50 (m, 2H), 2.17 (m, 2H° C.), 1.48 (s, 6H).

Workup

  1. customA white precipitate formed
  2. filtrationwhich was filtered off
  3. washwashed with water
  4. customdried (485 mg, 76%)

Sources & evidence

ORD record
ord-4ea7081d4fe34e2a925dc1a4570a11f7
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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