Tetrahydrofuran → HCID 178431748, compound

HRID 1618736Notes

Reaction equation

HRID 1618736 reaction equation
[NH2:1][C:2]1([CH:11]=[CH:10][CH:9]=[N:8][CH2:7]1)C(OC)=O.C(OC)(=[O:15])CC.CC(C)([O-])C.[Na+].[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>>[CH3:11][C:10]1[C:9]([OH:15])=[N:8][C:7]2[C:25]([C:26]=1[OH:27])=[CH:24][CH:28]=[N:1][CH:2]=2

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 11124Methyl propionateHCID 23676156Sodium t-butoxideHCID 67285060HCID 67285060, compound

Product 1

HCID 178431748HCID 178431748, compound

Conditions

Temperature
100 °C

Procedure

To a stirred solution of methyl 3-aminonicotinate (2.0 g, 13.14 mmol) and methyl propionate (30.9 mL, 329 mmol) in THF (30 mL) was added sodium tert-butoxide (3.16 g, 32.9 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 precipitate was filtered and dried under vacuum overnight to give 3-methyl-1,7-naphthyridine-2,4-diol. 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 precipitate was filtered
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-138093b1367940f8a1e0ecc271a61402
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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