Methyl propionate → HCID 178431750, compound

HRID 1431705Notes

Reaction equation

HRID 1431705 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(C)([O-])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

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 tert-butoxide (2.053 g, 21.36 mmol) portion wise over 1 min. The reaction was stirred at rt for 40 min and then 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. waitat 100° C. for 4 h
  2. temperatureAfter this time the reaction was cooled to rt
  3. customevaporated in vacuo
  4. dissolutionThe resulting solid was dissolved in water (20 mL)
  5. filtrationThe resulting solid was filtered
  6. customdried under vacuum overnight

Sources & evidence

ORD record
ord-8f693e57e3b74f52bd0cca2805d202e2
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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