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

HRID 840944Notes

Reaction equation

HRID 840944 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): δ12.35 (s, 1H); 8.12 (m, 1H); 7.90 (m, 1H); 7.14 (m, 1H); 5.75 (s, 2H). Electrospray MS m/a 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-4d8b20ecc7b5463899929013c55b8eb4
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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