Acetic Acid → HCID 2803813, compound

HRID 1578696Notes

Reaction equation

HRID 1578696 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[CH3:10][O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1.C(O)(=O)C.[OH-].[K+]>O>[CH3:10][O:11][C:12]1[CH:18]=[CH:17][C:15]([N:16]2[CH:3]=[CH:7][CH:6]=[CH:5]2)=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 667934-Methoxy-2-nitroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 2803813HCID 2803813, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 g (0.75 mole) of 2,5-dimethoxytetrahydrofuran are added to a solution of 84.1 g (0.5 mole) of 4-methoxy-2-nitroaniline in 500 ml. of glacial acetic acid. The solution is refluxed for 30 minutes, poured into 2500 ml. of water, and neutralized with potassium hydroxide. A solid precipitates and is filtered, dried, and recrystallized from ether to give 1-(4-methoxy-2-nitrophenyl)pyrrole, m.p. 75.5°-76.5° C.

Workup

  1. temperatureThe solution is refluxed for 30 minutes
  2. additionpoured into 2500 ml
  3. customA solid precipitates
  4. filtrationis filtered
  5. customdried
  6. customrecrystallized from ether

Sources & evidence

ORD record
ord-ca975fabc1e94650ab2c1a05e40c3412
Source dataset
uspto-grants-1976_02
Patent number
US03939159

Reaction notes

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