Ammonia → HCID 178519929, compound

HRID 1601817Notes

Reaction equation

HRID 1601817 reaction equation
[C:1]([OH:5])(=O)[CH2:2]O.[Cl:6][C:7]1[N:12]=[C:11]([NH2:13])[C:10]([NH2:14])=[CH:9][CH:8]=1.Cl.N>>[Cl:6][C:7]1[N:12]=[C:11]2[NH:13][C:2]([CH2:1][OH:5])=[N:14][C:10]2=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 757Glycolic AcidHCID 106306156-Chloropyridine-2,3-diamine

Product 1

HCID 178519929HCID 178519929, compoundYield 83.4%

Conditions

Temperature
150 °C

Procedure

6.60 g of glycolic acid were added to 5.00 g of 6-chloro-2,3-diaminopyridine (prepared as described in Preparation 42), and the resulting mixture was stirred at 150° C. for 4 hours. At the end of this time, the reaction mixture was treated with 3 N aqueous hydrochloric acid and subsequently made alkaline by the addition of aqueous ammonia. The aqueous mixture was evaporated to dryness, and the resulting residue was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of ethyl acetate and methanol in ratios ranging from 1:0 to 10:1 by volume as the eluent. The product was then crystallized by trituration with ethyl acetate, to give 5.33 g of the title compound, melting at 224-226° C.

Workup

  1. customThe aqueous mixture was evaporated to dryness
  2. customthe resulting residue was purified by column chromatography through silica gel
  3. washa gradient elution method
  4. customThe product was then crystallized by trituration with ethyl acetate

Sources & evidence

ORD record
ord-f90be834a6a248a5b4cc42654ebcb9bc
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

Loading…