Methanol → (E)-ethyl 3-(4-acetamido-3-(2-methoxyethoxy)phenylamino)-2-cyanoacrylate

HRID 403652ノート

反応式

HRID 403652 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[NH:15][C:16](=[O:18])[CH3:17].CO.[H][H].[C:23](/[C:25](=[CH:31]\OCC)/[C:26]([O:28][CH2:29][CH3:30])=[O:27])#[N:24]>[Pd].C1COCC1.C1(C)C=CC=CC=1.C(O)(=O)C>[C:16]([NH:15][C:7]1[CH:8]=[CH:9][C:10]([NH:12]/[CH:31]=[C:25](\[C:23]#[N:24])/[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:11][C:6]=1[O:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:18])[CH3:17]

参加物

9

反応物 4

HCID 887MethanolHCID 1715183Ethyl 2-cyano-3-ethoxyacrylateHCID 67287383N-(2-(2-methoxyethoxy)-4-nitrophenyl)acetamideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 67474100(E)-ethyl 3-(4-acetamido-3-(2-methoxyethoxy)phenylamino)-2-cyanoacrylate収率 75.1%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To N-(2-(2-methoxyethoxy)-4-nitrophenyl)acetamide (75 g, 0.295 mol, 1.00 equiv) was added methanol (600 ml), 10% Pd/C (6 g), and glacial acetic acid (60 ml) in a vessel which subject to a closed pressure vessel. Replacement of Kettle access from air to 5 atm hydrogen at room temperature was deployed and reacted for 5 hours. The reaction mixture was filtered, and concentrated. Toluene (440 ml), THF (220 ml), and (E)-ethyl 2-cyano-3-ethoxyacrylate (76 g, 0.497 mol, 1.68 equiv) were added and then refluxed for 16 h. The reaction mixture was cooled to room temperature, filtered, washed and dried with tetrahydrofuran to give 77 g product as off-white solid. MS (ESI) m/z: 347 (M+1).

後処理

  1. customsubject to a closed pressure vessel
  2. customat room temperature
  3. customreacted for 5 hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated
  6. temperaturerefluxed for 16 h
  7. filtrationfiltered
  8. washwashed
  9. dry with materialdried with tetrahydrofuran

出典と根拠

ORDレコード
ord-c3276314a347489790600ba719f9412d
出典データセット
uspto-grants-2014_06
特許番号
US08748453B2

反応ノート

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