Benzo(h)cinnolin-3(2H)-one, 5,6-dihydro- → 3-Chloro-5,6-dihydrobenzo[h]cinnoline

HRID 1400095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400095
[N:1]1[NH:2][C:3](=O)[CH:4]=[C:5]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[CH2:7][CH2:6]2.O(Cl)[Cl:17].[P+3]>>[Cl:17][C:3]1[N:2]=[N:1][C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1

Komponenten

3

Edukt 2

HCID 213230Benzo(h)cinnolin-3(2H)-one, 5,6-dihydro-HCID 178479710HCID 178479710, Verbindung

Produkt 1

HCID 104433233-Chloro-5,6-dihydrobenzo[h]cinnoline

Versuchsvorschrift

5,6-Dihydrobenzo[h]cinnolin-3(2H)-one (4.5 g) was heated at 100° C. with phosphorus (III) Oxychloride (80 mL) for 6.5 h. The solvent was removed under vacuum and the residue was treated with ice water. The resulting solid was filtered off, washed well with water and air dried to give 3-chloro-5,6-dihydrobenzo[h]cinnoline; 1H NMR (DMSO-d6, 300 MHz) 8.32 (m, 1H), 7.36 (s, 1H), 7.32 (m, 2H), 7.19 (d, 1H), 2.91 (s, 4H) ppm; MS (ES) 217/219 (M+H).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. additionthe residue was treated with ice water
  3. filtrationThe resulting solid was filtered off
  4. washwashed well with water and air
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6d7ff7af32d7463c9fd09201078c0757
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906922B2

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