Phosphorus oxychloride → 4-Chloro-7-methoxy-2-phenylquinoline

HRID 1815693ノート

反応式

HRID 1815693 の反応式
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178487676HCID 178487676、化合物

生成物 1

HCID 107544774-Chloro-7-methoxy-2-phenylquinoline

実験手順

The product of Step 1a (21.7 g, 86.4 mmole) was suspended in POCl3 (240 mL). The suspension was refluxed for 2 hours. After removal of the POCl3 in vacuo, the residue was partitioned between EtOAc (IL), and cold aqueous NaOH (generated from 1.0N 200 mL NaOH and 20 mL 10.0 N NaOH) and stirred for 15 min. The organic layer was washed with water (2×200 mL), brine (200 mL), dried (MgSO4), and concentrated in vacuo to supply 4-chloro-2-phenyl-7-methoxyquinoline (21.0 g, 90%) as a light brown solid. 1H NMR (DMSO-d6) δ: 3.97 (s, 3H), 7.36 (dd, J=9.2, 2.6 Hz, 1H), 7.49-7.59 (m, 4H), 8.08 (d, J=9.2 Hz, 1H), 8.19 (s, 1H), 8.26-8.30 (m, 2H); 13C NMR (DMSO-d6) δ: 55.72, 108.00, 116.51, 119.52, 120.48, 124.74, 127.26, 128.81, 130.00, 137.58, 141.98, 150.20, 156.65, 161.30. LC-MS (retention time: 1.547, Method D), MS m/z 270 (M++1).

後処理

  1. temperatureThe suspension was refluxed for 2 hours
  2. customAfter removal of the POCl3 in vacuo
  3. customthe residue was partitioned between EtOAc (IL), and cold aqueous NaOH (generated from 1.0N 200 mL NaOH and 20 mL 10.0 N NaOH)
  4. washThe organic layer was washed with water (2×200 mL), brine (200 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo to supply 4-chloro-2-phenyl-7-methoxyquinoline (21.0 g, 90%) as a light brown solid

出典と根拠

ORDレコード
ord-a01e5a84fc6b4569a8a0c17a3da99576
出典データセット
uspto-grants-2005_04
特許番号
US06878722B2

反応ノート

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