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

HRID 2414741Notes

Reaction equation

HRID 2414741 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-954c43abf28a43ac81de29cd9175f280
Source dataset
uspto-grants-2004_11
Patent number
US06815439B2

Reaction notes

Loading…