Hydrochloric Acid → 1H,2H,3H-pyrrolo[2,3-c]pyridin-2-one hydrochloride

HRID 840932Notes

Reaction equation

HRID 840932 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[NH2:12])C.[ClH:14]>CCOCC>[ClH:14].[NH:12]1[C:7]2[C:6](=[CH:11][CH:10]=[N:9][CH:8]=2)[CH2:5][C:4]1=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12407502Ethyl (3-aminopyridin-4-yl)acetate

Product 1

HCID 219562271H,2H,3H-pyrrolo[2,3-c]pyridin-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 50-ml round-bottom flask was added 0.36 g (2.0 mmol) of 3-amino-4-pyridineacetic acid ethyl ester, 15 mL of ether and 10 mL of 10% hydrochloric acid. The resulting biphasic solution was stirred for 16 hours at room temperature. The two phases were separated, and the ether phase was washed with 5 mL of water. The combined aqueous phases were evaporated to dryness to yield 0.285 g of the title compound as a brown solid. 1H NMR (DMSO-d6): δ5.93 (s, 1H), 7.59 (d, J=5.6 Hz, 1H), 8.02 (s,1H), 8.49 (d, J=5.6 Hz, 1H), 12.54 (s, 1H), 14.0 (bs, 1H); C8H6N2O: APCI+MS: m/z 135 (M+H).

Workup

  1. customThe two phases were separated
  2. washthe ether phase was washed with 5 mL of water
  3. customThe combined aqueous phases were evaporated to dryness

Sources & evidence

ORD record
ord-c8a20c8136584e24bd5658c9447005bf
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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