Nitrogen → N-(3-Nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide

HRID 383615

反応式

HRID 383615 の反応式
N#N.CCN(CC)CC.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH2:22][CH2:23][C:24]([OH:26])=O)[CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19].[N+:27]([C:30]1[CH:31]=[C:32]([NH2:36])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N+:27]([C:30]1[CH:31]=[C:32]([NH:36][C:24](=[O:26])[CH2:23][CH2:22][C:14]2[CH:15]=[C:16]([O:20][CH3:21])[C:17]([O:18][CH3:19])=[C:12]([O:11][CH3:10])[CH:13]=2)[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]

参加物

7

反応物 4

HCID 947NitrogenHCID 74233-NitroanilineHCID 8471TriethylamineHCID 648603,4,5-Trimethoxyhydrocinnamic acid

生成物 1

HCID 9411047N-(3-Nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide収率 70.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

(The following reaction is done in an anhydrous N2 atmosphere.) Suspend EDCHCl (402 mg, 2.10 mmol) and Et3N (2934, 2.10 mmol) in anhydrous DCM (17 mL) and stir the resulting solution for 5 min at rt. Add 3-(3,4,5-Trimethoxy-phenyl)-propionic acid (480 mg, 2.00 mmol) and DMAP (24 mg, 0.20 mmol) and stir the resulting solution for 5 min. 3-Nitro-phenylamine (88) (414 mg, 3.00 mmol) and stir the reaction solution 24 h at rt. Quench reaction solution with sat. aqu. NH4Cl and water, separate layers and extract aqu. layer with EtOAc (3 times). Wash combined organic layer with brine and dry with Na2SO4. Purify the crude product by preparative radial chromatography (silica gel, EtOAc/CyH 1+1) to obtain N-(3-Nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide (89) (508 mg, 70%) as a yellow solid. 1H NMR (400 MHz, CDCl3): 2.65 (t, 2H, J=7.5 Hz); 2.98 (t, 2H, J=7.5 Hz); 3.79 (s, 6H); 3.81 (s, 3H); 6.42 (s, 2H); 7.41 (s, 1H); 7.45 (t, 1H, J=8.3 Hz); 7.84 (d, 1H, J=8.3 Hz); 7.92 (d, 1H, J=8.3 Hz); 8.31 (s, 1H).

後処理

  1. custom(The following reaction
  2. customQuench
  3. customreaction solution with sat. aqu
  4. customNH4Cl and water, separate layers
  5. extractionextract aqu
  6. washWash
  7. dry with materialdry with Na2SO4
  8. customPurify the crude product by preparative radial chromatography (silica gel, EtOAc/CyH 1+1)

出典と根拠

ORDレコード
ord-d8e77fd563424791ab53415908df9065
出典データセット
uspto-grants-2013_02
特許番号
US08367677B2

関連ノート

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