Hydrochloric Acid → HCID 14390445, compound

HRID 2351779Notes

Reaction equation

HRID 2351779 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=[C:9]([Cl:23])[N:8]=1)C.O.[OH-].[K+].Cl>C(O)CO>[Cl:23][C:9]1[N:8]=[C:7]2[N:6]([CH2:5][C:4]([OH:3])=[O:24])[C:14]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[N:13][C:12]2=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 15617222HCID 15617222, compound

Product 1

HCID 14390445HCID 14390445, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of N-[6-chloro-3-[(4-chlorobenzoyl)amino]-2-pyridinyl]glycine ethyl ester (1.7 g, 0.00462 mole) in ethylene glycol (25 ml) was refluxed under nitrogen for two hours. To one-half of the solution (0.0023 mole) was added water (2 ml) and solid potassium hydroxide (0.20 g, 0.003515 mole) and the mixture was refluxed for an additional 15 minutes, poured into ice water (100 ml) and acidified with 3 N hydrochloric acid solution. The resulting solid was collected by filtration, rinsed with water, dissolved in hot methanol and filtered hot. Addition of water to the collected by filtration, washed with water, and dried at 60° C. under high vacuum to give 0.4 g (54% yield) of title compound, mp >250° C.

Workup

  1. temperaturethe mixture was refluxed for an additional 15 minutes
  2. filtrationThe resulting solid was collected by filtration
  3. washrinsed with water
  4. dissolutiondissolved in hot methanol
  5. filtrationfiltered hot
  6. additionAddition of water to the
  7. filtrationcollected by filtration
  8. washwashed with water
  9. customdried at 60° C. under high vacuum

Sources & evidence

ORD record
ord-99a64a95f90c4c4caaa077a397e933f2
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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