Phosphoric Acid → HCID 178428356, compound

HRID 1728574Notes

Reaction equation

HRID 1728574 reaction equation
[CH:1]1([C:4](O)=O)[CH2:3][CH2:2]1.P(=O)(O)(O)O.[NH2:12][C:13]1[C:18]([NH2:19])=[C:17]([CH3:20])[CH:16]=[CH:15][N:14]=1.[OH-].[K+]>O>[CH:1]1([C:4]2[NH:12][C:13]3=[N:14][CH:15]=[CH:16][C:17]([CH3:20])=[C:18]3[N:19]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 14797Potassium HydroxideHCID 15655Cyclopropanecarboxylic acidHCID 3174954-Methylpyridine-2,3-diamine

Product 1

HCID 178428356HCID 178428356, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

30 ml of cyclopropanecarboxylic acid and 70 ml of phosphoric acid (85%) were added to 15 g of 2,3-diamino-4-methylpyridine, and the mixture was stirred at an internal temperature of 130° C. for 12 hr. The reaction mixture was cooled, poured into a solution of 140 g of potassium hydroxide in 420 ml of water and then extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by column chromatography (chloroform:ethanol=97:3). The yield was 14.1 g, and the product was recrystallized from ethyl acetate-isopropyl ether to prepare the title compound in a pure form having a melting point of 203° to 204° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (chloroform:ethanol=97:3)
  6. customThe yield was 14.1 g, and the product was recrystallized from ethyl acetate-isopropyl ether
  7. customto prepare the title compound in a pure form

Sources & evidence

ORD record
ord-a63b072eeb0c4bb28d9c0fcf2e0f4e29
Source dataset
uspto-grants-1994_07
Patent number
US05328911

Reaction notes

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