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Potassium Hydroxide → 2-(2',6'-Difluorophenyl)-1,8-naphthyridine

HRID 830
Notes
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Reaction equation

HRID 830 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]([C:13]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[F:20])=O.[OH-].[K+]>CO>[F:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([F:20])[C:13]=1[C:11]1[CH:10]=[CH:4][C:3]2[C:2](=[N:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 836431-(2,6-Difluorophenyl)ethan-1-oneHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 157902082-(2',6'-Difluorophenyl)-1,8-naphthyridineYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Aminonicotinaldehyde (2.44 g, 20 mmol) and 2,6-difluoroacetophenone (3.28 g, 21 mmol) are dissolved in 20 ml of MeOH. The mixture is treated dropwise with 3 ml of 40% KOH and, after the exothermic reaction has subsided, it is poured onto water and the residue which is deposited is filtered off with suction. 3.8 g (79% yield) of the desired product are obtained. M.p. 100°-103° C.

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. customafter the exothermic reaction
  2. additionit is poured onto water
  3. filtrationthe residue which is deposited is filtered off with suction

Sources & evidence

ORD record
ord-819df65591774363bb9b76f5effae47b
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723413

Reaction notes

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