1-Chloro-3-iodopropane → 3-(3-chloropropyl)-1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one

HRID 1922360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922360
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:21])=[CH:5][CH:4]=1.CC(C)=O.C(=O)=O.CC1(C)[SiH2][SiH]=NC(C)(C)C1(C)C.[Li].I[CH2:45][CH2:46][CH2:47][Cl:48]>C1COCC1.C(Cl)Cl>[Cl:48][CH2:47][CH2:46][CH2:45][CH:10]1[CH2:11][C:12]2[C:17](=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=2)[C:9]1=[O:21]

Komponenten

7

Edukt 4

HCID 813631-Chloro-3-iodopropaneHCID 18522661Acetone cardiceHCID 598070541-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-oneHCID 131729715Lithium hexamethyldisilazine

Produkt 1

HCID 598071463-(3-chloropropyl)-1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (350 mg, 1.12 mmol) in 10 mL THF was cooled to −78° C. (acetone/dry ice bath) then treated with lithium hexamethyldisilazine (1.23 mL of a 1M solution in THF). The resulting dark solution was stirred for 30 minutes then treated with 1-iodo-3-chloropropane dropwise. The mixture was allowed to warm to room temperature and kept at this temperature overnight. The reaction was quenched with brine and extracted with 3×50 mL CH2Cl2. The combined organic fractions were dried over MgSO4, filtered and concentrated to give a dark residue which was subjected to flash chromatography on silica gel using CH2Cl2. A yellow viscous oil was obtained (130 mg, 29.8%). 1H-NMR (CDCl3) δ: 8.08-8.00 (m, 2H), 7.12-7.09 (m, 2H), 7.00 (d, J=8.7 Hz, 1H), 6.86-6.84 (m, 2H), 5.15 (dd, J=4.2, 20.4 Hz, 2H), 3.76 (s, 3H), 3.60 (t, J=6.3 Hz, 2H), 3.17 (dd, J=5.4, 15.6 Hz, 1H), 2.93-2.71 (m, 2H), 2.05-1.67 (m, 4H).

Aufarbeitung

  1. customkept at this temperature overnight
  2. customThe reaction was quenched with brine
  3. extractionextracted with 3×50 mL CH2Cl2
  4. dry with materialThe combined organic fractions were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a dark residue which
  8. customA yellow viscous oil was obtained (130 mg, 29.8%)

Quellen und Nachweise

ORD-Eintrag
ord-9cc66681ab97471faabf86a053654451
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173813B2

Notizen zur Reaktion

Wird geladen…