Ammonium Chloride → HCID 58036800, Verbindung

HRID 1952002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1952002
[C:1]1([P:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][CH3:25].[NH4+].[Cl-]>C1COCC1>[C:18]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[NH:16][CH:15]([CH3:25])[CH:14]=[CH:13]3)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 6286598-(Diphenylphosphino)quinolineHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 58036800HCID 58036800, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 8-diphenylphoshinoquinoline (1) (10 g, 31.95 mmol) in dry THF (150 mL) under nitrogen was added MeLi (39.9 mL, 1.6 M in diethyl ether, 1 mmol) at −78° C. and the solution was stirred at 0° C. for 10 minutes. The solution was cooled down to −78° C., saturated aqueous NH4Cl solution (100 mL) was added and the mixture was warmed to room temperature. Products were extracted with EtOAc, washed with water and saturated aqueous NaCl, dried (MgSO4) and evaporated to give 2 as a yellow oil, which solidified on standing (10.5 g, quantitative). 1H NMR (400.13 MHz, CDCl3) δ 7.4-7.25 (m, 10H, Ph-H), 6.86 (dd, 1H, J=7.2, 1.2, C5—H), 6.63 (ddd, 1H, J=7.6, 6.0, 1.6 Hz, C7—H), 6.49 (t, 1H, J=7.6 Hz, C6—H), 6.29 (d, 1H, J=9.6 Hz, C4—H), 5.54 (ddd, 1H, J=10.0, 4.0, 2.0 Hz, C3—H), 4.71 (d, 1H, J=7.6 Hz, N1—H), 4.35 (m, 1H, C2—H), 1.15 (d, 3H, J=6.4 Hz, C1′—CH3) ppm; 13C NMR (100.61 MHz, CDCl3) δ 147.0 (d, J=18.2 Hz), 135.5 (d, J=13.1 Hz), 135.4 (d, J=12.1 Hz), 134.2 (d, J=5.1 Hz), 133.4 (d, J=18.2 Hz), 133.3 (d, J=18.2 Hz), 128.5 (d, J=11.1 Hz), 128.4 (d, J=12.1 Hz), 128.0, 117.0, 116.1, 48.2, 24.2 ppm; 31P NMR (161.97 MHz, CDCl3) δ −23.2 ppm.

Aufarbeitung

  1. temperatureThe solution was cooled down to −78° C.
  2. temperaturethe mixture was warmed to room temperature
  3. extractionProducts were extracted with EtOAc
  4. washwashed with water and saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-40456db2c2c34e648d971f40bb87f7fd
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404843B2

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