Hydrochloric Acid → 1H-Pyrrolo[2,3-c]pyridine-7-carboxylic acid

HRID 639529Notes

Reaction equation

HRID 639529 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][CH:8]=[C:9]2[CH:13]=[CH:12][NH:11][C:10]=12)=[O:4].[OH-].[K+].Cl>C1COCC1>[NH:11]1[C:10]2=[C:5]([C:3]([OH:4])=[O:2])[N:6]=[CH:7][CH:8]=[C:9]2[CH:13]=[CH:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68576910Methyl 1H-pyrrolo[2,3-C]pyridine-7-carboxylate

Product 1

HCID 534130241H-Pyrrolo[2,3-c]pyridine-7-carboxylic acidYield 156.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1H-Pyrrolo[2,3-c]pyridine-7-carboxylic acid methyl ester (example E1, 50 mg, 0.28 mmol) was dissolved in THF (0.57 mL) and treated with 2 M aq. potassium hydroxide solution (0.57 mL, 1.1 mmol), then after 1 h acidified with 2M aq. hydrochloric acid solution and extracted with dichloromethane. The aqueous layer was evaporated and the residue was taken up in methanol and the residue was taken up in methanol and filtered. The filtrate was evaporated to afford the title compound (71 mg), which contained an unspecified amount of potassium chloride. MS (EI) 118.1 (100), 162.1 (53, M+); 1H-NMR (300 MHz, CD3OD): 8.30-8.25 (m, 2H), 8.24 (d, J=3.0, 1H), 7.07 (d, J=3.0, 1H).

Workup

  1. extractionextracted with dichloromethane
  2. customThe aqueous layer was evaporated
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-44f0609a39114296b392b978973fc75f
Source dataset
uspto-grants-2010_04
Patent number
US07691876B2

Reaction notes

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