Ammonia → 3-(6-Nitro-2-quinolinyl)-3,9-diazabicyclo[3.3.1]nonane

HRID 2246423Notes

Reaction equation

HRID 2246423 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH:9]1[CH2:10][N:11]([C:17]1[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([N+:27]([O-:29])=[O:28])[CH:23]=3)[N:18]=1)[CH2:12]2)=O)(C)(C)C.FC(F)(F)C(O)=O.N>>[N+:27]([C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([N:11]1[CH2:10][CH:9]3[NH:8][CH:13]([CH2:14][CH2:15][CH2:16]3)[CH2:12]1)[CH:26]=[CH:25]2)([O-:29])=[O:28]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 68622090HCID 68622090, compound

Product 1

HCID 247812953-(6-Nitro-2-quinolinyl)-3,9-diazabicyclo[3.3.1]nonane

Procedure

A mixture of 3-(6-nitro-quinolin-2-yl)-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (0.6 g, 1.51 mmol), prepared by method A and trifluoroacetic acid (1.7 g, 15.1 mmol) was stirred for 10 min at room-temperature. Aqueous ammonia was added and the mixture was extracted with dichloromethane. The mixture was dried and evaporated followed by stirring in diethylether and filtration. Yield 320 mg (71%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customThe mixture was dried
  3. customevaporated
  4. stirringby stirring in diethylether
  5. filtrationfiltration

Sources & evidence

ORD record
ord-08b8dd286cd443659b76f0281a6d50b4
Source dataset
uspto-grants-2010_03
Patent number
US07687517B2

Reaction notes

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