Sodium Hydroxide → HCID 12414839, compound

HRID 1657411Notes

Reaction equation

HRID 1657411 reaction equation
[CH3:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9]1([CH3:32])[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH:23]([C:29]([CH3:31])=O)[C:24](OCC)=[O:25])[CH2:17][CH2:16]2)[CH:10]=1.[OH-].[Na+]>O>[C:9]1([CH3:32])[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][C:23]3[C:24](=[O:25])[N:4]4[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]4=[N:8][C:29]=3[CH3:31])[CH2:19][CH2:20]2)[CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 153472-Amino-3-methylpyridineHCID 12414943HCID 12414943, compound

Product 1

HCID 12414839HCID 12414839, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.19 g of 3-methyl-2-aminopyridine, 1 g of ethyl 2-[2-(4-m-tolyl-1-piperazinyl)ethyl]acetoacetate and 1.17 g of polyphosphoric acid was heated at 120° - 130°C for 2 hours. After completion of the reaction, water was added to the reaction mixture. The resulting mixture was made basic by addition of an aqueous sodium hydroxide solution and then extracted with ethyl acetate. After evaporation of the solvent from the extract, the remaining residue was washed with isopropyl alcohol and recrystallized from isopropyl alcohol to give 0.1 g of the desired compound as pale yellow needles, m.p. 106° - 106.5°C.

Workup

  1. temperaturewas heated at 120° - 130°C for 2 hours
  2. additionwas added to the reaction mixture
  3. extractionextracted with ethyl acetate
  4. customAfter evaporation of the solvent from the extract
  5. washthe remaining residue was washed with isopropyl alcohol
  6. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-8fc7296651394d2fbaf1f4102609a57d
Source dataset
uspto-grants-1976_06
Patent number
US03960863

Reaction notes

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