Methyl propionate → HCID 178431750, compound

HRID 1618730Notes

Reaction equation

HRID 1618730 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[C:12](OC)(=[O:15])[CH2:13][CH3:14].CC([O-])(C)C.[Na+]>C1COCC1>[CH3:14][C:13]1[C:12]([OH:15])=[N:1][C:2]2[C:3]([C:4]=1[OH:6])=[CH:8][CH:9]=[CH:10][N:11]=2

Participants

5

Reactant 3

HCID 11124Methyl propionateHCID 351633Methyl 2-aminopyridine-3-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 178431750HCID 178431750, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of methyl 2-aminonicotinate (1.3 g, 8.54 mmol) and methyl propionate (20.08 mL, 214 mmol) in THF (20 mL) was added sodium 2-methylpropan-2-olate (2.053 g, 21.36 mmol) portionwise over 1 min. The reaction was stirred at rt for 40 min and at 100° C. for 4 h. After this time the reaction was cooled to rt and evaporated in vacuo. The resulting solid was dissolved in water (20 mL) and neutralized to pH 7 with 1.0M aqueous HCl. The resulting solid was filtered and dried under vacuum overnight to give 3-methyl-1,8-naphthyridine-2,4-diol as a tan solid. Mass Spectrum (ESI) m/e=177.2 (M+1).

Workup

  1. temperatureAfter this time the reaction was cooled to rt
  2. customevaporated in vacuo
  3. dissolutionThe resulting solid was dissolved in water (20 mL)
  4. filtrationThe resulting solid was filtered
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-6431961390ce4c52a70bc2a898568091
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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