2-Chloro-6-nitroquinoline → Ammonia

HRID 2054699Notes

Reaction equation

HRID 2054699 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][C@@H:26]2[CH2:28][C@H:23]1[CH2:24][NH:25]2)=[O:21])([CH3:18])([CH3:17])[CH3:16]>O1CCOCC1>[NH3:3].[N+:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:25]1[CH2:24][C@@H:23]3[CH2:28][C@H:26]1[CH2:27][N:22]3[C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH:11]=[CH:10]2)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 109217232-Chloro-6-nitroquinolineHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 2

HCID 222AmmoniaHCID 69215243HCID 69215243, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-6-nitroquinoline [Lee B S, Lee B C, Jun J-G and Chi D Y; Heterocycles 1998 48 (12) 2637-2641] (2.1 g; 10 mmol), tert-butyl-(1S,4S)-(−)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (2.0 g; 10 mmol) and dioxane (50 ml) was stirred at reflux for 20 hours. The solvent was evaporated. Aqueous sodium hydroxide (50 ml; 1 M) was added, followed by extraction with diethyl ether (3×50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 1.6 g (43%).

Workup

  1. temperatureat reflux for 20 hours
  2. customThe solvent was evaporated
  3. additionAqueous sodium hydroxide (50 ml; 1 M) was added
  4. extractionfollowed by extraction with diethyl ether (3×50 ml)

Sources & evidence

ORD record
ord-e9a1d0d2c57d4ab89b8e7eafa8a00545
Source dataset
uspto-grants-2008_02
Patent number
US07329754B2

Reaction notes

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