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

HRID 1578691Notes

Reaction equation

HRID 1578691 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl: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]([Cl:9])[CH:15]=[CH:14][C:13]=1[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24489Sodium Dithionite3×HCID 10846711HCID 10846711, compound

Product 1

HCID 106554015-chloro-2-(1H-pyrrol-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

10 g of sodium hydrosulfite are added portionwise to a stirred solution of 10.0 g (0.045 mole) of 1-(4-chloro-2-nitrophenyl)pyrrole, 200 ml. of tetrahydrofuran and 100 ml. of water, and the solution is heated on a steam bath for 5 minutes. An additional 10 g of sodium hydrosulfite are added and the solution is again heated on a steam bath for 5 minutes. Then 23 g more of sodium hydrosulfite and a solution of 200 ml. of ethanol in 250 ml. of water are added and heated for 5 minutes on a steam bath. The organic solvents are distilled, leaving a suspension of a tan solid. The solid is filtered, washed with water, dried, and recrystallized from hexane to give yellow needles, m.p. 89°-90°C. of 1-(2-amino-4-chlorophenyl)pyrrole.

Workup

  1. temperaturethe solution is again heated on a steam bath for 5 minutes
  2. temperatureheated for 5 minutes on a steam bath
  3. distillationThe organic solvents are distilled
  4. customleaving
  5. additiona suspension of a tan solid
  6. filtrationThe solid is filtered
  7. washwashed with water
  8. customdried
  9. customrecrystallized from hexane

Sources & evidence

ORD record
ord-e28a018ce6b049f3991a446847de84b7
Source dataset
uspto-grants-1976_02
Patent number
US03939159

Reaction notes

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