Phenyl chloroformate → Phenyl methyl(2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

HRID 1922402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922402
[CH3:1][N:2](C)[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[C:19]1([O:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH3:1][N:2]([CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1)[C:26](=[O:27])[O:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 15891Phenyl chloroformateHCID 59807155N,N-Dimethyl-2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine

Produkt 1

HCID 57343232Phenyl methyl(2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamateAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of N,N-dimethyl-2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine (500 mg, 2.01 mmol) in 10 mL CH2Cl2 was treated dropwise with phenylchloroformate (378 μL, 3.01 mmol). The reaction was stirred at room temperature for 17 hours then partitioned between CH2Cl2 100 mL and 1N NaOH (20 mL). After extraction, the organic layer was separated, dried over Na2SO4, filtered and concentrated to give a yellow residue. This residue was subjected to flash chromatography on silica gel using 20% EtOAc/CH2Cl2 to give a yellow residue (610 mg, 85.4%). 1H-NMR (CDCl3) δ 7.99-7.92 (m, 1H), 7.87 (d, J=2.1 Hz, 1H), 7.39-7.33 (m, 2H), 7.23-7.19 (m, 1H), 7.06-7.01 (m, 2H), 6.69 (m, 1H), 3.67-3.52 (m, 4H), 3.48 (t, J=5.7 Hz, 2H), 3.14 and 3.07 (2×s, 3H), 2.79 (t, J=6.3 Hz, 2H), 1.99-1.96 (m, 2H). MS (ESI): 356.2 (M+1).

Aufarbeitung

  1. customthen partitioned between CH2Cl2 100 mL and 1N NaOH (20 mL)
  2. extractionAfter extraction
  3. customthe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow residue

Quellen und Nachweise

ORD-Eintrag
ord-d18c68375ca8413b9d8ea617ee0e56e6
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173813B2

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