Ammonium Hydroxide → HCID 21584325, compound

HRID 369960Notes

Reaction equation

HRID 369960 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[CH2:3][CH:4]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:5]1[C:6]2=[O:11].[N+:17]([O-])([O-:19])=[O:18].[K+].[OH-].[NH4+]>S(=O)(=O)(O)O>[N+:17]([C:9]1[CH:8]=[C:7]2[C:2]([CH2:3][CH:4]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:5]3[C:6]2=[O:11])=[CH:1][CH:10]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 215843408,9,10,11,11a,12-Hexahydroazepino[1,2-b]isoquinolin-5(7H)-one

Product 1

HCID 21584325HCID 21584325, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 8,9,10,11,11a,12-hexahydro-7H-azepino[1,2-b]isoquinolin-5-one (2.50 g, 11.6 mmol) in concentrated sulfuric acid (30 ml) at 0° C. was added in a single portion potassium nitrate (1.23 g, 12.2 mmol). After the reaction mixture had stirred overnight, it was poured onto ice and basified with concentrated ammonium hydroxide. The aqueous phase was extracted twice with dichloromethane, dried (magnesium sulfate), and concentrated to leave about 15 ml of solvent. Hexanes (100 ml) was added and the solution was placed in the freezer. The precipitated product was collected and dried to give the title compound as a yellow solid (1.94 g, 64%), m.p. 117.5-9° C.

Workup

  1. extractionThe aqueous phase was extracted twice with dichloromethane
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cb0c990a62f24a26b87d18aa9f08175d
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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