2-[(2-Chloro-4-nitrophenoxy)methyl]-6-methylpyridine → 3-Chloro-4-[(6-methylpyridin-2-yl)methoxy]aniline

HRID 222036ノート

反応式

HRID 222036 の反応式
[Cl:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:16]=[C:15]([CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)[NH2:17]

参加物

4

反応物 1

HCID 668773902-[(2-Chloro-4-nitrophenoxy)methyl]-6-methylpyridine

生成物 1

HCID 220552383-Chloro-4-[(6-methylpyridin-2-yl)methoxy]aniline収率 88.2%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

実験手順

2-[(2-chloro-4-nitrophenoxy)methyl]-6-methylpyridine (4.87 g, 17.5 mmol) and iron powder (4.87 g, 87.4 mmol) were mixed in 150 mL acetic acid, and were stirred at rt overnight. The reaction mixture was filtered through a pad of Celite®, and washed with EtOAc. The filtrate was concentrated in vacuo and neutralized with saturated Na2CO3 solution. The contents were extracted with EtOAc (5×300 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting crude material was triturated with Hex/EtOAc (2:1) to afford 3-chloro-4-[(6-methylpyridin-2-yl)methoxy]aniline (3.84 g, 88%) as a white solid. 1H-NMR (DMSO) δ 7.70 (dd, 1H), 7.31 (d, 1H), 7.17 (d, 1H), 6.88 (d, 1H), 6.65 (d, 1H), 6.44 (dd, 1H), 5.01 (s, 2H), 4.93 (s, 2H), 2.46 (s, 3H); LCMS RT=0.25 min; [M+H]+=249.2.

後処理

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. extractionThe contents were extracted with EtOAc (5×300 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting crude material was triturated with Hex/EtOAc (2:1)

出典と根拠

ORDレコード
ord-c1e1ad8661e743c0b5e9fa4b91a3d4e5
出典データセット
uspto-grants-2012_06
特許番号
US08207172B2

反応ノート

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