Potassium Hydroxide → HCID 12621377, compound

HRID 1730164Notes

Reaction equation

HRID 1730164 reaction equation
[CH3:1][C:2]1([CH3:23])[N:6]=[C:5]([C:7]2[CH:16]=[CH:15][C:10]([NH:11]C(=O)C)=[CH:9][CH:8]=2)[CH2:4][CH:3]1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[OH-].[K+]>C(O)C>[NH2:11][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[CH2:4][CH:3]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)[C:2]([CH3:23])([CH3:1])[N:6]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12621369HCID 12621369, compound

Product 1

HCID 12621377HCID 12621377, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.8 G. of 4'-[5,5-dimethyl-4-(4-pyridyl)-1-pyrrolin-2-yl]-acetanilide are treated with a solution of 5.8 g. of potassium hydroxide in 58 ml. of ethanol and heated under reflux for 5 hours. Then the reaction mixture is evaporated under reduced pressure and the residue is treated with water. The resulting crystals are filtered and washed well with water. The mineral is dried and recrystallized from methanol/ether to yield 4-[2-(p-aminophenyl)-5,5-dimethyl-1-pyrrolin-4-yl]-pyridine of melting point 175°-178° C. The hydrochloride, recrystallized from methanol/ether, has a melting point of 290°-300° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThen the reaction mixture is evaporated under reduced pressure
  3. additionthe residue is treated with water
  4. filtrationThe resulting crystals are filtered
  5. washwashed well with water
  6. customThe mineral is dried
  7. customrecrystallized from methanol/ether

Sources & evidence

ORD record
ord-aa082275266d45739376103b7d7829e3
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

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