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

HRID 531177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 531177
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-d6ba9eb7f87a43808d00ba41e8463c4f
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353126B2

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