Ammonium nitrate → HCID 66982354, compound

HRID 516260Notes

Reaction equation

HRID 516260 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16][C:13]=3[CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:28].[Br:29]N1C(=O)CCC1=O.[N+]([O-])([O-])=O.[NH4+]>C(#N)C>[Br:29][C:14]1[C:13]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:19][CH2:20][C:12]=2[CH:11]=[C:10]2[C:15]=1[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:7](=[O:28])[CH2:8][CH2:9]2

Participants

5

Reactant 3

HCID 22985Ammonium nitrateHCID 67184N-bromobutanimideHCID 66982553HCID 66982553, compound

Product 1

HCID 66982354HCID 66982354, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 150 mg of t-butyl 1-(3-methoxypropyl)-2-oxo-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate in 4.2 ml of acetonitrile were added 107 mg of N-bromosuccinimide and 3.7 mg of ammonium nitrate, followed by stirring at room temperature for 3.5 hours. The reaction mixture was concentrated to about ¼, and ethyl acetate, an aqueous sodium thiosulfate solution, and aqueous sodium bicarbonate was added thereto. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain 198 mg of t-butyl 11-bromo-1-(3-methoxypropyl)-2-oxo-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated to about ¼, and ethyl acetate
  2. additionan aqueous sodium thiosulfate solution, and aqueous sodium bicarbonate was added
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d59a7f52b59c4d95a3877723ba0e06e4
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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