Hydrazine → 2-Hydrazino-5,6-dihydrobenzo[h]quinazoline

HRID 1400093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400093
Cl[C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[CH:12]=[CH:13][CH:14]=[CH:15][C:5]=3[C:4]=2[N:3]=1.[NH2:16][NH2:17]>N1C=CC=CC=1>[NH:16]([C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[CH:12]=[CH:13][CH:14]=[CH:15][C:5]=3[C:4]=2[N:3]=1)[NH2:17]

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 534860272-Chloro-5,6-dihydrobenzo[h]quinazoline

Produkt 1

HCID 597745152-Hydrazino-5,6-dihydrobenzo[h]quinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Crude 2-chloro-5,6-dihydrobenzo[h]quinazoline was heated at 120° C. in a mixture of anhydrous pyridine (20 mL) and anhydrous hydrazine (7 mL) for 4 h. The solvent was removed under vacuum and the residue was partitioned between chloroform and 1M aqueous potassium carbonate solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 2-hydrazinyl-5,6-dihydrobenzo[h]quinazoline as a white solid, 2.16 g. 1H NMR (CDCl3, 300 MHz) 8.27 (d, 1H), 8.20 (s, 1H), 7.35 (m, 2H), 7.21 (d, 1H), 6.42 (s, 1H), 4.00 (br s, 2H), 2.91 (m, 2H), 2.80 (m, 2H) ppm; 13C NMR (CDCl3, 75 MHz) 164.29, 160.00, 156.72, 139.87, 132.83, 131.02, 128.25, 127.25, 125.47, 119.03, 28.54, 24.24; MS (ES) 213 (M+H).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between chloroform and 1M aqueous potassium carbonate solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a8c27fd403294bd0b92cb77e737a1b5a
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906922B2

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