Triethylamine → Ethyl 6-methoxy-1,5-naphthyridine-3-carboxylate

HRID 2279288Notes

Reaction equation

HRID 2279288 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[N:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=2)=[O:5])[CH3:2].C(N(CC)CC)C.C(OCC)(=O)C>[Pd].C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[N:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 23209173Ethyl 4-chloro-6-methoxy-1,5-naphthyridine-3-carboxylate

Product 1

HCID 66747245Ethyl 6-methoxy-1,5-naphthyridine-3-carboxylateYield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-chloro-6-methoxy-[1,5]naphthyridine-3-carboxylic acid ethyl ester (75 g, 241.86 mmol, 1.0 eq), triethylamine (75 mL, 538.08 mmol, 2.22 eq), and 10% palladium on activated carbon (8.2 g) in ethanol (1350 mL) is stirred under hydrogen flow at room temperature for 6 hours. The catalyst is then removed by filtration and the solution is evaporated to dryness to give a yellow solid as crude product, which is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 5:1, v/v) to afford 6-methoxy-[1,5]naphthyridine-3-carboxylic acid ethyl ester as a light yellow powder (46.2 g, 77% yield).

Workup

  1. customThe catalyst is then removed by filtration
  2. customthe solution is evaporated to dryness
  3. customto give a yellow solid as crude product, which
  4. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-895a0eadf9d74ef78bfea59881c3eb59
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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