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

HRID 383616

반응식

HRID 383616 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 887Methanol용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-9ede8fb8e0f041c595165695f309931d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367677B2

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