Hydrochloric Acid → 1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarboxylic acid

HRID 2169425Notes

Reaction equation

HRID 2169425 reaction equation
[N:1]1([C:10]2([C:15]#N)[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.O[Li].[OH2:19].C(OCC)(=[O:22])C.Cl>O.CCCCCC>[N:1]1([C:10]2([C:15]([OH:22])=[O:19])[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 152225521-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonitrile

Product 1

HCID 867260551-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonitrile (393) (6.2 g, 29.35 mmol) in water (90 mL) was added LiOH.H2O (14 g, 334.56 mmol). The reaction mixture was refluxed for 24 h (TLC, 30% ethyl acetate in hexane, Rf=0.3). It was thereafter cooled to 0° C. and the aqueous part was acidified with HCl (6N) to pH 3 and extracted with ethyl acetate (3×50 mL). The organic phase was thereafter dried and concentrated to get 1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarboxylic acid (394) (5.8 g, 86%) as an off-white solid.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. customThe organic phase was thereafter dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ea5058d450fa4389ba7c7861070fc870
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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