Ammonium Chloride → HCID 58036800, 화합물

HRID 1515170노트

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HRID 1515170 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 58036800HCID 58036800, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c3885c9ac16d499cba7d6d65c6bcc6a0
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222415B2

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