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

HRID 383616

反応式

HRID 383616 の反応式
N#N.[N+:3]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:28])[CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)[CH:9]=[CH:10][CH:11]=1)([O-])=O>CO.[Pd]>[NH2:3][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:28])[CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)[CH:9]=[CH:10][CH:11]=1

参加物

5

反応物 2

HCID 947NitrogenHCID 9411047N-(3-Nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide

生成物 1

HCID 16225054N-(3-Amino-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide収率 99%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 887Methanol溶媒

実験手順

(The following reaction is done in an N2 atmosphere.) Dissolve N-(3-Nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide (89) (100 mg, 0.28 mmol) in MeOH (4.5 mL) and add Pd on carbon (10% (w/w) Pd content, 29.5 mg, 0.028 mmol) followed by NH4CO2H (175 mg, 2.77 mmol) at rt. Degas the reaction mixture carefully (flush with N2) and stir it for 75 min at rt. Filtrate reaction mixture through a short pad of celite and remove solvent. Treat residue with EtOAc, filtrate again through a short pad of celite and remove solvent to obtain N-(3-Amino-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide (90) (91 mg, 99%) as a white solid. No further purification. 1H NMR (400 MHz, CD3OD): 2.65 (t, 2H, J=7.5 Hz); 2.98 (t, 2H, J=7.5 Hz); 3.75 (s, 3H); 3.82 (s, 6H); 6.50 (dd, 1H, J1=8.0 Hz, J2=2.0 Hz); 6.58 (s, 2H); 6.80 (dd, 1H, J=8.0 Hz, J2=2.0 Hz); 7.02-7.07 (m, 1H); 7.04 (t, 1H, J=8.0 Hz).

後処理

  1. custom(The following reaction
  2. customfollowed by NH4CO2H (175 mg, 2.77 mmol) at rt
  3. customDegas
  4. customthe reaction mixture carefully (flush with N2)
  5. customFiltrate reaction mixture through a short pad of celite
  6. customremove solvent
  7. customTreat residue with EtOAc, filtrate again through a short pad of celite and remove solvent

出典と根拠

ORDレコード
ord-9ede8fb8e0f041c595165695f309931d
出典データセット
uspto-grants-2013_02
特許番号
US08367677B2

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