Nitric Acid → HCID 19760205, compound

HRID 1586910Notes

Reaction equation

HRID 1586910 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([CH3:18])([CH3:17])[CH2:9][CH2:8][C:7]1=[O:19]>C(OC(=O)C)(=O)C.C(O)(=O)C>[CH3:5][N:6]1[C:12]2[CH:13]=[CH:14][C:15]([N+:1]([O-:4])=[O:2])=[CH:16][C:11]=2[C:10]([CH3:17])([CH3:18])[CH2:9][CH2:8][C:7]1=[O:19]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 197602442,3,4,5-tetrahydro-1,5,5-trimethyl-2-oxo-1H-1-benzazepine

Product 1

HCID 19760205HCID 19760205, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent2×

Procedure

2.0 ml of 65% nitric acid were cautiously added dropwise to 7.1 ml of acetic anhydride at 0° C. This solution was added to a solution of 3.14 g of 2,3,4,5-tetrahydro-1,5,5-trimethyl-2-oxo-1H-1-benzazepine in 9.0 ml of acetic anhydride and 2.8 ml of glacial acetic acid. The reaction mixture was left to stand at room temperature for 3 days and then poured on ice, washed in succession with water, soda solution and water, dried and evaporated. Recrystallization from ethyl acetate/hexane yielded 3.39 g of 2,3,4,5-tetrahydro-1,5,5-trimethyl-7-nitro-2-oxo-1H-1-benzazepine, 113°-115° C.

Workup

  1. waitThe reaction mixture was left
  2. additionpoured on ice
  3. washwashed in succession with water, soda solution and water
  4. customdried
  5. customevaporated
  6. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f53b199fc7874cd3be7cabb152462ad5
Source dataset
uspto-grants-1993_06
Patent number
US05216148

Reaction notes

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