Ammonia → 2-(3,8-Diaza-bicyclo[3.2.1]oct-3-yl)-6-nitro-quinoline

HRID 645352Notes

Reaction equation

HRID 645352 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([C:16]1[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=3)[N:17]=1)[CH2:12]2)=O)(C)(C)C.FC(F)(F)C(O)=O.N>ClCCl>[CH:13]12[NH:8][CH:9]([CH2:15][CH2:14]1)[CH2:10][N:11]([C:16]1[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=3)[N:17]=1)[CH2:12]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 686830833-(6-Nitro-quinolin-2-yl)-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 119507832-(3,8-Diaza-bicyclo[3.2.1]oct-3-yl)-6-nitro-quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(6-nitro-quinolin-2-yl)-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (1.0 g, 2.6 mmol), trifluoroacetic acid (2.97 g, 26.0 mmol) and dichloromethane (10 ml) was stirred for 15 h. The mixture was made alkaline by adding concentrated ammonia. The mixture was extracted with dichloromethane, dried and evaporated. Yield 0.50 g (90%) Mp 185° C. decomp.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-5da7f429d1c04681b8419faefc4a3a8b
Source dataset
uspto-grants-2010_04
Patent number
US07704991B2

Reaction notes

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