Stannous Chloride → HCID 10623989, compound

HRID 1815482Notes

Reaction equation

HRID 1815482 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][C:25]2=[O:29])=[O:19])=[CH:12][C:11]=1[N+:30]([O-])=O.Cl[Sn]Cl>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][C:25]2=[O:29])=[O:19])=[CH:12][C:11]=1[NH2:30]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 9957380HCID 9957380, compound

Product 1

HCID 10623989HCID 10623989, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of nitro compound (780 mg, 1.58 mmol) from Example 33, SnCl2 (1.50 g, 7.91 mmol) in 25 mL of anhydrous EtOH was refluxed under nitrogen atmosphere for 90 minutes. The reaction was then allowed to cool to room temperature, quenched with sat. NaHCO3, extracted with EtOAc.(2×50 mL). The combined organic layer was washed with water and brine, dried over Na2SO4, condensed in vacuo to give the crude aniline as yellowish brown solid, which was converted to the bromide without purification.

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 90 minutes
  2. customquenched with sat. NaHCO3
  3. extractionextracted with EtOAc
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4, condensed in vacuo

Sources & evidence

ORD record
ord-913273ce6808415ab31a7842c9a2e3b8
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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