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Methanol → ethyl 2-(5-oxo-1,6-naphthyridin-6(5H)-yl)acetate

HRID 219274
Notes
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Reaction equation

HRID 219274 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][N:7]=[C:6]([OH:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.I[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].CO>C1COCC1>[O:11]=[C:6]1[N:7]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[CH:9][C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]1=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 12183Ethyl iodoacetateHCID 178517692HCID 178517692, compound

Product 1

HCID 58015535ethyl 2-(5-oxo-1,6-naphthyridin-6(5H)-yl)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
100 °C

Procedure

1,6-naphthyridin-5-ol (1.00 g, 6.8 mmol), ethyl iodoacetate (1.6 ml, 14 mmol) and cesium carbonate (4.5 g, 14 mmol) were dissolved in 25 mL of THF then stirred and heated at 100° C. for 2 h until the reaction was complete. The reaction was concentrated and purified via MPLC using a gradient to 90% DCM: 10% MeOH to afford ethyl 2-(5-oxo-1,6-naphthyridin-6(5H)-yl)acetate (1.5 g, 94% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified via MPLC

Sources & evidence

ORD record
ord-e4ccbd0856c048dba118d4c56b7c5abe
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08198448B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes