Citric Acid → HCID 57421979, compound

HRID 2108752Notes

Reaction equation

HRID 2108752 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[S:14][C:13]([C:15]([O:17]CC)=[O:16])=[CH:12][CH:11]=2)=[CH:2]1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.C(OCC)(=O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=2)=[CH:2]1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 57421980HCID 57421980, compound

Product 1

HCID 57421979HCID 57421979, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 5-(1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-2-carboxylate (0.89 g, 3.3 mmol) was partly dissolved in 1,4 dioxane and 10 mL 1N NaOH added. The reaction mixture was heated to 80° C. where it became homogenous. After 2 hours the reaction mixture was cooled to room temperature, diluted with ethyl acetate, and a 10% citric acid solution. A precipitate formed which was filtered off, washed with water and dried to 0.71 g, 2.9 mmol, 88% yield.

Workup

  1. temperatureAfter 2 hours the reaction mixture was cooled to room temperature
  2. customA precipitate formed which
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried to 0.71 g, 2.9 mmol, 88% yield

Sources & evidence

ORD record
ord-02402a8cafc1426eb2315e4ad8239dde
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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