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

HRID 1267811Notes

Reaction equation

HRID 1267811 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8e8222c305244f06a7c8890eb29d23ae
Source dataset
uspto-grants-2003_04
Patent number
USRE038103E1

Reaction notes

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