Nitrogen → 8-(2-Nitrobenzenesulfonyl)amino-5,6,7,8-tetrahydroquinoline

HRID 251278

Reaktionsgleichung

Reaktionsgleichung von HRID 251278
[N:1]1[C:10]2[CH:9]([NH2:11])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21](Cl)(=[O:23])=[O:22])([O-:14])=[O:13].CCN(CC)CC.N#N>C1COCC1>[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([NH:11][CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)(=[O:23])=[O:22])([O-:14])=[O:13]

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 113555648-Amino-5,6,7,8-tetrahydroquinoline

Produkt 1

HCID 226013948-(2-Nitrobenzenesulfonyl)amino-5,6,7,8-tetrahydroquinolineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5,6,7,8-tetrahydro-quinolin-8-ylamine (1.73 g, 12.0 mmol) dissolved in THF (80 mL) was added 2-nitrobenzenesulfonyl chloride (2.92 g, 13.0 mmol) and Et3N (2.4 mL, 18.0 mmol). The mixture was stirred for 16 hours at room temperature under a positive pressure of N2. The reaction mixture was quenched with saturated aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (2×100 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to afford 2-nitro-N-(5,6,7,8-tetrahydro-quinolin-8-yl)-benzenesulfonamide as a dark brown solid (3.72 g, 94%). 1H NMR (CDCl3) δ 1.59 (m, 1H), 1.89 (m, 2H), 2.50 (m, 1H), 2.76 (m, 2H), 4.35 (m, 1H), 6.86 (m, 1H), 7.04 (m, 1H), 7.35 (m, 1H), 7.74 (m, 2H), 7.99 (m, 1H), 8.12 (m, 1H), 8.26 (m, 1H).

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated aqueous NaHCO3 (100 mL)
  2. extractionextracted with CH2Cl2 (2×100 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a9c5e2e1760f47e799985dad479dcc3c
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863293B2

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