Tetrahydrofuran → 4-Biphenylsulfonic acid, 4'-amino-

HRID 29494

Reaction equation

HRID 29494 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.[Sn](Cl)Cl.C1COCC1>O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([OH:19])(=[O:17])=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24479Stannous ChlorideHCID 534258824'-Nitro-4-biphenylsulfonic acid

Product 1

HCID 957994-Biphenylsulfonic acid, 4'-amino-Yield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4′-Nitro-biphenyl-4-sulfonic acid (1.12 g, 4 mmol) was mixed with tin (II) chloride (5.2 g, 32 mmol) and 40 ml of THF. The mixture was refluxed overnight. The reaction mixture was poured into 80 ml of water and stirred at room temperature for 8 h. The mixture was filtered and the solid was dried under vacuum to provide 0.73 g (73%) of 4′-amino-biphenyl-4-sulfonic acid, obtained as an off-white solid.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThe mixture was filtered
  3. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-a520dcafb84945c88476d716e5caae5b
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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