Diethyl Malonate → 5-chloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

HRID 2394329Notes

Reaction equation

HRID 2394329 reaction equation
[NH2:1][C:2]1[C:3]([CH:9](C(OCC)=O)[C:10]([O:12]CC)=O)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.NC1C(Cl)=NC(C(C(OCC)=O)C(OCC)=O)=CC=1.C(OCC)(=O)CC(OCC)=O>Cl>[Cl:8][C:5]1[N:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:10](=[O:12])[CH2:9]2

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 105173603-Amino-6-bis(ethoxycarbonyl)methyl-2-chloropyridineHCID 105893293-Amino-2-bis(ethoxycarbonyl)methyl-6-chloropyridine

Product 1

HCID 106546885-chloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The mixture containing 3-amino-2-bis(ethoxycarbonyl)methyl-6-chloropyridine, 3-amino-6-bis(ethoxycarbonyl)methyl-2-chloropyridine and diethyl malonate was taken up in 6N HCl solution (700 mL) and heated at reflux for 5 hours. After removing the aqueous acid in vacuo, the residue was taken up in water and again concentrated to yield 5-chloro-4-azaoxindole as a brown solid which was dried in the air. The yield was 7.04 g. (32% overall from 2,6-dichloro-3-nitropyridine). An analytical sample was prepared by recrystallization from isopropanol; m.p. 250°-254° C. (dec.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. customAfter removing the aqueous acid in vacuo
  4. concentrationagain concentrated

Sources & evidence

ORD record
ord-040800c009b843f88f1782ad86d73ea9
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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