Ammonium Chloride → 5-Amino-6-(2,4-difluorophenylthio)-1-indanone

HRID 1451542ノート

反応式

HRID 1451542 の反応式
C1O[C:4]2([C:12]3[C:7](=[CH:8][C:9]([N+:22]([O-])=O)=[C:10]([S:13][C:14]4[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=4[F:21])[CH:11]=3)[CH2:6][CH2:5]2)[O:3]C1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:22][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[S:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])[C:4](=[O:3])[CH2:5][CH2:6]2

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 103167575-Nitro-6-(2,4-difluorophenylthio)-1-indanone ethylene ketal

生成物 1

HCID 102662765-Amino-6-(2,4-difluorophenylthio)-1-indanone収率 88.5%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 19096565Water ethanol溶媒

実験手順

A mixture of 5-nitro-6-(2,4-difluorophenylthio)-1-indanone ethylene ketal (580 mg, 1.59 mmol), iron powder (500 mg, 8.9 mmol) and ammonium chloride (50 mg, 0.93 mmol) in 30 mL of ethanol:water (2:1) was refluxed for 1 h. The hot mixture was filtered through celite. The solvente was evaporated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The ethyl acetate extract was dried over anhydrous MgSO4 and concentrated to give the title compound (410 mg, 81%) as a light brown solid. 1H NMR (CDCl3) δ7.95 (s, 1H), 7.00 (m, 1H), 6.80 (m, 2H), 6.72 (s, 1H), 4.95 (br s, 2h), 3.05 (t, 2H), 2.65 (t, 2H).

後処理

  1. temperaturewas refluxed for 1 h
  2. filtrationThe hot mixture was filtered through celite
  3. customThe solvente was evaporated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. dry with materialwas dried over anhydrous MgSO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-8038d0f02efc452b92a38534b33b6523
出典データセット
uspto-grants-1997_02
特許番号
US05604260

反応ノート

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