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

HRID 1267811노트

반응식

HRID 1267811 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 19096565Water ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8e8222c305244f06a7c8890eb29d23ae
출처 데이터셋
uspto-grants-2003_04
특허 번호
USRE038103E1

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