Water → Quinoline

HRID 857272Notes

Reaction equation

HRID 857272 reaction equation
[N+](C1C=C([C:10]2[CH:11]=[C:12](CC3C=CN=CC=3)[CH:13]=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[CH:15]3)C=CC=1)([O-])=O.O.[NH4+].[Cl-]>CCO.[Fe]>[N:18]1[C:19]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 98193566-(4-Pyridylmethyl)-8-(3-nitrophenyl)quinoline

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of the 8-(3-nitro-phenyl)-6-pyridin-4-ylmethyl-quinoline (1.0 eq) described in Step 1 in EtOH (0.2M) at 60° C. was added of water (final concentration 0.15M) and saturated aqueous NH4Cl (1.3 eq) followed by iron (12 eq). The final mixture was stirred at 60° C. for 2 h, cooled to room temperature, filtered on celite and concentrated to afford the title compound as a yellow solid.

Workup

  1. filtrationfiltered on celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c20e2479fed5484581f295c73f5418af
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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