Hydrochloric Acid → 2-Methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxylic acid

HRID 1612469Notes

Reaction equation

HRID 1612469 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([O:11]C(C)(C)C)=[O:10])[CH:6]=[C:5]([N:16]2[CH2:20][CH2:19][CH2:18][C:17]2=[O:21])[N:4]=1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[C:5]([N:16]2[CH2:20][CH2:19][CH2:18][C:17]2=[O:21])[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22252983t-Butyl 2-methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxylate

Product 1

HCID 222530372-Methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

t-Butyl 2-methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxylate (D57) (0.27 g) was stirred overnight in a dioxan solution of HCl (4M; 10 mL). The solution was evaporated to dryness and dissolved in sat. aq. sodium bicarbonate. The basic aqueous solution was washed twice with ether and was then acidified to pH4 with citric acid solution (10% aq.), saturated with NaCl and extracted three times with ethyl acetate. The combined extracts were washed with brine, dried and evaporated to a solid which was triturated with water, collected by filtration and dried at 50° C. in vacuo (silica gel desiccant). The title compound (D58) was obtained as an off-white solid (0.141 g).

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutiondissolved in sat. aq. sodium bicarbonate
  3. washThe basic aqueous solution was washed twice with ether
  4. extractionextracted three times with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. customdried
  7. customevaporated to a solid which
  8. customwas triturated with water
  9. filtrationcollected by filtration
  10. customdried at 50° C. in vacuo (silica gel desiccant)

Sources & evidence

ORD record
ord-aecc84ac612b42df8ca01712cd73b4cb
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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