Ethanol → 2-Tert-butyl-5-chloro-1,6-naphthyridine

HRID 921031Notes

Reaction equation

HRID 921031 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[C:6]([NH2:10])[CH:5]=[CH:4][N:3]=1.[CH3:11][C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=O.N1CCCCC1.C(O)C>ClCCl>[C:14]([C:12]1[CH:11]=[CH:8][C:7]2[C:6](=[CH:5][CH:4]=[N:3][C:2]=2[Cl:1])[N:10]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 6416PinacoloneHCID 8082PiperidineHCID 454898674-Amino-2-chloronicotinaldehyde

Product 1

HCID 772308302-Tert-butyl-5-chloro-1,6-naphthyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 15.7 g (100 mmol) of 2-chloro-3-formyl-4-aminopyridine [338452-92-9], 37.6 ml (300 mmol) of tert-butyl methyl ketone, 1.0 ml (10 mmol) of piperidine and 100 ml of ethanol is heated under reflux for 60 h. After cooling, the reaction mixture is diluted with 500 ml of dichloromethane, washed five times with 500 ml of water each time, dried over magnesium sulfate, and the solvent is removed in vacuo. The residue is recrystallised from ethanol. Yield: 8.2 g (37 mmol), 37%. Purity: >95% according to 1H-NMR.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 60 h
  3. temperatureAfter cooling
  4. washwashed five times with 500 ml of water each time
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent is removed in vacuo
  7. customThe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-ae9003b46fec4341a1279b29dc69caa6
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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