Potassium Hydroxide → tert-Butyl 3-(1,8-naphthyridin-2-yl)propylcarbamate

HRID 379238Notes

Reaction equation

HRID 379238 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][CH2:10][C:11](=O)[CH3:12])([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[C:21]([CH:22]=O)=[CH:20][CH:19]=[CH:18][N:17]=1.[OH-].[K+]>C(O)C>[N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:22]=[CH:12][C:11]=1[CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:14]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 21478928tert-Butyl (4-oxopentyl)carbamate

Product 1

HCID 11369698tert-Butyl 3-(1,8-naphthyridin-2-yl)propylcarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 11-4 (5.0 g, 24.8 mmol), 1-3, 2-amino-3-formylpyridine (3.6 g, 29.8 mmol) and 20% KOH (1 ml) in absolute ethanol (100 mL) was heated at reflux for 8 h. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 70:28:2 chloroform/ethyl acetate/methanol) to give 11-6 as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, 70:28:2 chloroform/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-0c35a855b4814796ad1aab9352f0fa78
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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