Ammonia → 3-Methoxy-2,7-naphthyridine

HRID 1441492Notes

Reaction equation

HRID 1441492 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]#[C:12][Si](C)(C)C)[C:6]([CH:7]=O)=[CH:5][N:4]=1.[NH3:17]>CO>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[C:9]([CH:10]=1)=[CH:11][CH:12]=[N:17][CH:7]=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59164393HCID 59164393, compound

Product 1

HCID 591643983-Methoxy-2,7-naphthyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Methoxy-4-[(trimethylsilyl)ethynyl]-nicotinaldehyde (0.25 g, 1.1 mmol) and 7M ammonia in MeOH (5 mL) were stirred in a sealed vial at 80° C. overnight. The solution was concentrated, taken up in saturated sodium carbonate and extracted with ether. The organic phase was dried, filtered and concentrated to give 0.20 g of the title product.

Workup

  1. concentrationThe solution was concentrated
  2. extractionextracted with ether
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-821f15c03eb8474f8d0b8f797c401166
Source dataset
uspto-grants-2010_02
Patent number
US07655664B2

Reaction notes

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