Stannous Chloride → HCID 10623989, compound

HRID 984464Notes

Reaction equation

HRID 984464 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 down 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 (2×50 mL)
  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-f3c8aa6366be4d6fbcce696f3af01af5
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

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