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

HRID 1508079ノート

反応式

HRID 1508079 の反応式
[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]

参加物

4

反応物 1

HCID 13475730N-Methyl-4-nitrobenzeneethanesulfonamide

生成物 1

HCID 134757684-Amino-N-methylbenzeneethanesulfonamide収率 90%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-83808cc5813940f59baec2c593a6c646
出典データセット
uspto-grants-2015_12
特許番号
US09221797B2

反応ノート

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