N-Methyl-4-nitrobenzeneethanesulfonamide → 4-Amino-N-methylbenzeneethanesulfonamide

HRID 1508079노트

반응식

HRID 1508079 반응식
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)(=[O:5])=[O:4]>CO.[Pd]>[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)(=[O:4])=[O:5]

참가 물질

4

반응물 1

HCID 13475730N-Methyl-4-nitrobenzeneethanesulfonamide

생성물 1

HCID 134757684-Amino-N-methylbenzeneethanesulfonamide수율 90%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A solution of 402 mg (1.65 mmol) of 2-(4-nitro-phenyl)-ethanesulfonic acid methylamide (as prepared in the previous step) in MeOH (30 mL) was hydrogenated over 10% Pd/C (Degussa type E101-NE/W, Aldrich, 50% by weight water) at 20 psi of H2 for 19 h. The reaction mixture was filtered through Celite, and the filter cake was washed with MeOH. Solvents were evaporated in vacuo. Silica gel chromatography of the residue on a 25-g Varian MegaBond Elut SPE column with 50% EtOAc-hexane afforded 318 mg (90%) of the title compound as a white solid: 1H-NMR (CD3CN; 400 MHz): δ 7.01 (d, 2H, J=8.4 Hz), 6.61 (d, 2H, J=8.4 Hz), 5.00-4.92 (br s, 1H), 4.12-4.02 (br s, 2H), 3.24-3.17 (m, 2H), 2.92-2.86 (m, 2H), 2.67 (s, 3H, J=5.2 Hz).

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH
  3. customSolvents were evaporated in vacuo

출처 및 근거

ORD 기록
ord-83808cc5813940f59baec2c593a6c646
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221797B2

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