Ammonia → HCID 10087900, compound

HRID 1583757Notes

Reaction equation

HRID 1583757 reaction equation
Cl.[NH2:2][C:3]1[C:8]([NH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:6]=[C:5]([NH:15][CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[N:4]=1.N.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[NH2:2][C:3]1[C:8]([NH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:6]=[C:5]([NH:15][CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[N:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 311Citric AcidHCID 20258332HCID 20258332, compound

Product 1

HCID 10087900HCID 10087900, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

40 grams of 2-amino-3-carbethoxyamino-6-(2,4,6-trimethylbenzylamino)-pyridine hydrochloride were dissolved in 200 ml of methanol and treated with 25% aqueous ammonia, whereupon the base crystallized out. The base was filtered off with suction and dissolved in dioxane/methanol (2:1 by volume) in the hot. The warm solution was acidified with a solution of citric acid in methanol to pH 3, whereupon the "citrate" precipitated in cooling with stirring. The compound crystallized with 0.33 mole of citric acid and was recrystallized from a little isopropanol.

Workup

  1. customcrystallized out
  2. filtrationThe base was filtered off with suction
  3. dissolutiondissolved in dioxane/methanol (2:1 by volume) in the hot
  4. customprecipitated
  5. temperaturein cooling
  6. customwas recrystallized from a little isopropanol

Sources & evidence

ORD record
ord-b1a233cbfa6c4b0f811955600ecbc38f
Source dataset
uspto-grants-1985_11
Patent number
US04554281

Reaction notes

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