1-(chloromethyl)-5-nitro-3-[(5-nitroindol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indole → [5-amino-1-(chloromethyl)-1,2-dihydrobenzo[e]indol-3-yl]-(5-amino-1H-indol-2-yl)methanone

HRID 366807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 366807
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([N+:16]([O-])=O)=[CH:7][C:6]=2[N:5]([C:19]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][C:26]([N+:30]([O-])=O)=[CH:25][CH:24]=3)=[O:20])[CH2:4]1>C1COCC1.O=[Pt]=O>[NH2:16][C:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[C:11]2[CH:3]([CH2:2][Cl:1])[CH2:4][N:5]([C:19]([C:21]3[NH:22][C:23]4[C:28]([CH:29]=3)=[CH:27][C:26]([NH2:30])=[CH:25][CH:24]=4)=[O:20])[C:6]=2[CH:7]=1

Komponenten

4

Edukt 1

HCID 232899531-(chloromethyl)-5-nitro-3-[(5-nitroindol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indole

Produkt 1

HCID 392736[5-amino-1-(chloromethyl)-1,2-dihydrobenzo[e]indol-3-yl]-(5-amino-1H-indol-2-yl)methanoneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of the preceding dinitro compound 14b (170 mg, 0.38 mmol) in THF (120 mL) was hydrogenated over PtO2 at 50 psi for 2 h. After removal of the catalyst, the solution was concentrated to a small volume under reduced pressure below 25° C. and diluted with iPr2O to give 15b (136 mg, 92%), mp >300° C. 1H NMR [(CD3)2SO] δ 11.23 (d, J=1.4 Hz, 1 H, NH), 8.07 (d, J=8.4 Hz, 1 H, H-6), 7.75 (d, J=8.2 Hz, 1 H, H-9), 7.70 (s, 1 H, H-4), 7.45 (t, J=7.5 Hz, 1 H, H-8), 7.27 (t, J=7.7 Hz, 1 H, H-7), 7.21 (d, J=8.6 Hz, 1 H, H-7'), 6.88 (d, J=1.8 Hz, 1 H, H-3'), 6.76 (d, J=1.8 Hz, 1 H, H-4'), 6.68 (dd, J=8.6, 2.1 Hz, 1 H, H-6'), 5.96 (s, 2 H, dihydroindole NH2), 4.70 (dd, J=10.9, 8.9 Hz, 1 H, H-2), 4.64 (br, s, 2 H, indole NH2), 4.49 (dd, J=11.0, 1.6 Hz, 1 H, H-2), 4.15-4.07 (m, 1 H, H-1), 3.97 (dd, J=11.0, 3.0 Hz, 1 H, CHHCl), 3.74 (dd, J=11.0, 8.0 Hz, 1 H, CHHCl).

Aufarbeitung

  1. customAfter removal of the catalyst
  2. concentrationthe solution was concentrated to a small volume under reduced pressure below 25° C.
  3. additiondiluted with iPr2O

Quellen und Nachweise

ORD-Eintrag
ord-84c3946de83440caa3baf5e96d2cf436
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130237

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