2-Fluoro-5-nitrobenzene-1-sulfonamide → 5-amino-2-fluorobenzenesulfonamide

HRID 2408370ノート

反応式

HRID 2408370 の反応式
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][C:10]=1[F:11])(=[O:4])=[O:3]>ClCCl.CO.[Pd]>[NH2:12][C:7]1[CH:8]=[CH:9][C:10]([F:11])=[C:5]([S:2]([NH2:1])(=[O:3])=[O:4])[CH:6]=1

参加物

5

反応物 1

HCID 77303242-Fluoro-5-nitrobenzene-1-sulfonamide

生成物 1

HCID 432553875-amino-2-fluorobenzenesulfonamide収率 77.9%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-aminosulfonyl-4-fluoronitrobenzene (360 mg, 1.62 mmol) in dichloromethane (6 mL) and methanol (3 mL) was added 10% Pd/C (36 mg) and shaken under a hydrogen atmosphere at 50 psi for 15 minutes. The mixture was filtered through Celite and the cake was washed with methanol (5 mL). The combined organic solvent was concentrated under reduced pressure to give crude product, which was further purified by flash column chromatography (ethyl acetate:hexanes 1:1) to give 240 mg of 5-amino-2-fluorobenzensulfonamide as a light yellow solid. 1H NMR (DMSO-d6): δ 7.38 (s, 2H), 7.03-6.94 (m, 2H), 6.70-6.66 (m, 1H), 5.33 (s, 1H).

後処理

  1. filtrationThe mixture was filtered through Celite
  2. washthe cake was washed with methanol (5 mL)
  3. concentrationThe combined organic solvent was concentrated under reduced pressure
  4. customto give crude product, which
  5. customwas further purified by flash column chromatography (ethyl acetate:hexanes 1:1)

出典と根拠

ORDレコード
ord-85d2b673606641e7a337254ed44cd0aa
出典データセット
uspto-grants-2014_08
特許番号
US08815848B2

反応ノート

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