Ammonium Chloride → HCID 67469719, compound

HRID 407964Notes

Reaction equation

HRID 407964 reaction equation
[F:1][C:2]1[C:3]([N+:11]([O-])=O)=[CH:4][C:5]2[CH2:9][CH2:8][S:7][C:6]=2[CH:10]=1.[NH4+].[Cl-]>C(O)C.C1COCC1.[Fe]>[F:1][C:2]1[C:3]([NH2:11])=[CH:4][C:5]2[CH2:9][CH2:8][S:7][C:6]=2[CH:10]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 15856685HCID 15856685, compound

Product 1

HCID 67469719HCID 67469719, compoundYield 94.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-fluoro-5-nitro-2,3-dihydrobenzo[b]thiophene (2.1 g, 10.5 mmol) in ethanol (80 mL), THF (40 mL), and aqueous NH4Cl (20 mL) was added Fe (O) (3.53 g, 63.3 mmol). The mixture was refluxed for 2 hours, then filtered through celite and washed with ethyl acetate. The residue was purified using silica gel column chromatography with 50% ethyl acetate in hexanes to provide 6-fluoro-2,3-dihydrobenzo[b]thiophen-5-amine (1.68 g, 94.2% yield).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. filtrationfiltered through celite
  3. washwashed with ethyl acetate
  4. customThe residue was purified

Sources & evidence

ORD record
ord-9be5d141b5da407faf5e84880ffb50ab
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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