Hydrochloric Acid → 6-Chloro-1,3-dihydropyrrolo[3,2-B]pyridin-2-one

HRID 2394331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2394331
[NH2:1][C:2]1[C:3]([CH:9](C(OCC)=O)[C:10]([O:12]CC)=O)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>>[Cl:8][C:6]1[CH:7]=[C:2]2[C:3]([CH2:9][C:10](=[O:12])[NH:1]2)=[N:4][CH:5]=1

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 106132393-Amino-2-bis(ethoxycarbonyl)methyl-5-chloropyridine

Produkt 1

HCID 104873236-Chloro-1,3-dihydropyrrolo[3,2-B]pyridin-2-one

Versuchsvorschrift

A mixture of 3-amino-2-bis(ethoxycarbonyl)methyl-5-chloropyridine and 6N HCl (325 mL) was heated at reflux for 4 hours. After removing the aqueous acid in vacuo, the residue was taken up in water and filtered to remove a small amount of black insoluble material. On adjustment of the filtrate to pH 6.5 with solid NaHCO3, 6-chloro-4-azaoxindole precipitated as a tan solid (2.6 g) which was collected by filtration. The filtrate was extracted with ethyl acetate and the combined extracts were dried (MgSO4) and concentrated to yield an additional quantity of 6-chloro-4-azaoxindole (3.6 g). The total yield was thus 6.2 g (71% overall from 2,5-dichloro-3-nitropyridine).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customAfter removing the aqueous acid in vacuo
  4. filtrationfiltered
  5. customto remove a small amount of black insoluble material
  6. customOn adjustment of the filtrate to pH 6.5 with solid NaHCO3, 6-chloro-4-azaoxindole precipitated as a tan solid (2.6 g) which
  7. filtrationwas collected by filtration
  8. extractionThe filtrate was extracted with ethyl acetate
  9. dry with materialthe combined extracts were dried (MgSO4)
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-be18176633a84d18974f14a021a9c25b
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811432

Notizen zur Reaktion

Wird geladen…