Tetrahydrofuran → 5-methyl-2-(1H-pyrrol-1-yl)aniline

HRID 1578694Notes

Reaction equation

HRID 1578694 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)=[C:12]([N+:21]([O-])=O)[CH:11]=1.O1CCCC1>O.C(O)C>[NH2:21][C:12]1[CH:11]=[C:10]([CH3:9])[CH:15]=[CH:14][C:13]=1[N:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24489Sodium Dithionite3×HCID 28038101-(4-methyl-2-nitrophenyl)-1H-pyrrole

Product 1

HCID 27767955-methyl-2-(1H-pyrrol-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

20 g of sodium hydrosulfite are added portionwise to a solution of 18.18 g (0.09 mole) of 1-(4-methyl-2-nitrophenyl)pyrrole in 400 ml. of tetrahydrofuran and 200 ml. of water. The resulting solution is heated on a steam bath for 5 minutes and an additional 20 g. of sodium hydrosulfite are added and the solution is heated for 5 minutes on a steam bath. Then 38.3 g. of sodium hydrosulfite and a solution of 400 ml. of ethanol and 500 ml. of water are added, and again the solution is heated on a steam bath for 5 minutes. The solvent is removed to give a tan solid which is recrystallized from hexane to give white crystals, m.p. 89°-90° C. of 1-(2-amino-4-methylphenyl)pyrrole.

Workup

  1. temperatureThe resulting solution is heated on a steam bath for 5 minutes
  2. temperaturethe solution is heated for 5 minutes on a steam bath
  3. temperatureagain the solution is heated on a steam bath for 5 minutes
  4. customThe solvent is removed
  5. customto give a tan solid which
  6. customis recrystallized from hexane

Sources & evidence

ORD record
ord-d22d888adbdf446db4bd65ee3b835a75
Source dataset
uspto-grants-1976_02
Patent number
US03939159

Reaction notes

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