Hydrochloric Acid → 1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

HRID 1168235Notes

Reaction equation

HRID 1168235 reaction equation
[NH2:1][C:2]1[C:3]([CH2:8][C:9]([O:11]CC)=O)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl>C(OCC)C>[NH:1]1[C:2]2[C:3](=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:8][C:9]1=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15475339Ethyl 2-(3-aminopyridin-2-yl)acetate

Product 1

HCID 3163671,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-oneYield 78.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 2-(3-amino-pyridin-2-yl)-acetate (6.94 g, 0.038 mol) was dissolved in diethyl ether (100 mL) at room temperature. Hydrochloric acid (2M, 35 mL) was added, and the reaction was stirred for 30 minutes. The volatiles were removed to afford a brown solid that was recrystallized from ethanol and diethyl ether to provide the title compound (4.0 g, 62% yield). 1H NMR 400 MHz (DMSO-d6): δ 12.35 (s, 1H); 8.12 (m, 1H); 7.90 (m, 1H); 7.14 (m, 1H); 5.75 (s, 2H). Electrospray MS m/z 135 (M+H).

Workup

  1. customThe volatiles were removed
  2. customto afford a brown solid that
  3. customwas recrystallized from ethanol and diethyl ether

Sources & evidence

ORD record
ord-622837f737a64eb09b02c9713636e05f
Source dataset
uspto-grants-2003_09
Patent number
US06624171B1

Reaction notes

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