Pyridine → Ethyl 4-(3-naphthalen-2-yl-acryloylamino)benzoate

HRID 2422936ノート

反応式

HRID 2422936 の反応式
N1C=CC=CC=1.[NH2:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1/[CH:29]=[CH:30]/[C:31](Cl)=[O:32]>C(Cl)Cl>[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH:29]=[CH:30][C:31]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][CH:18]=1)=[O:32]

参加物

5

反応物 3

HCID 1049PyridineHCID 2337BenzocaineHCID 11830880(E)-3-(2-naphthyl)propenoyl chloride

生成物 1

HCID 67243223Ethyl 4-(3-naphthalen-2-yl-acryloylamino)benzoate収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Anhydrous pyridine (0.331 g, 4.2 mmol, 1.2 eq) and ethyl 4-aminobenzoate (0.577 g, 3.50 mmol) were added to a solution of (E)-3-(2-naphthyl)propenoyl chloride (prepared from its corresponding acid) (0.757 g, 3.50 mmo) in anhydrous DCM (15 ml) under Ar. After stirring overnight at room temperature, the white precipitate was filtered, washed with DCM (10 ml) and dried under vacuum to give the amide 42 (0.960 g, 2.78 mmol, 80%) as a white solid, mp 173-175° C. 1H NMR (400 MHz, DMSO-d6) δ 1.30 (3H, t, J 7.2 Hz), 4.28 (2H, t, J 7.2 Hz), 6.97 (1H, d, J 15.4 Hz), 7.54-7.57 (2H, m), 7.7 (1H, d, J 15.4 Hz), 7.77 (1H, dd, J 1.6, 9.2 Hz), 7.84 (2H, d, J 8.8 Hz), 7.93-7.97 (5H, m), 8.15 (1H, s), 10.58 (1H, bs). 13C NMR (100 MHz, DMSO-d6) δ 14.88, 61.09, 119.30, 122.91, 124.18, 124.99, 127.47, 127.83, 128.38, 129.09, 129.36, 130.05, 130.98, 132.82, 133.68, 134.26, 141.64, 144.33, 164.69, 166.01. νmax (solid)/(cm−1) 3357, 1702, 1660, 1619, 1607, 1591, 1521, 1403, 1282. MS (API-ES): m/z 346 [M+H]+ (100%), HRMS (API-ES) m/z found 346.1443 [M+H]+.

後処理

  1. filtrationthe white precipitate was filtered
  2. washwashed with DCM (10 ml)
  3. customdried under vacuum

出典と根拠

ORDレコード
ord-114f9e51929f4924a34c69cf59a14a9d
出典データセット
uspto-grants-2011_06
特許番号
US07960434B2

反応ノート

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