1,4-Dibromo-2-nitrobenzene → HCID 62896872, Verbindung

HRID 1817893

Reaktionsgleichung

Reaktionsgleichung von HRID 1817893
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl.[NH2:13][CH2:14][C:15]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:13][CH2:14][C:15]2([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Komponenten

5

Edukt 3

HCID 770041,4-Dibromo-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 211096931-(Aminomethyl)cyclopentan-1-ol--hydrogen chloride (1/1)

Produkt 1

HCID 62896872HCID 62896872, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

The mixture of 2,5-dibromonitrobenzene (Tokyo Kasei Kogyo Co., Ltd., 5.4 g, 19.2 mmol), 1-(aminomethyl)cyclopentanol hydrochloride (J. Med. Chem. 1981, 24, 12-16, 4.3 g, 28.4 mmol) and N,N-diisopropylethylamine (8.4 mL, 48.1 mmol) in 1-methyl-2-pyrrolidinone (32 mL) was microwaved for 30 min at 200° C. The reaction was quenched with water and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent) to afford the title compound (2.6 g, 43%) as an orange amorphous solid.

Aufarbeitung

  1. customwas microwaved for 30 min at 200° C
  2. customThe reaction was quenched with water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-42a2a21addcc496abd29a1388410969d
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598393B2

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