Ethylene Glycol → 2-(3,4-dichlorophenyl)3H-imidazo[4,5-b]pyridine-3-acetic acid

HRID 621872Notes

Reaction equation

HRID 621872 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])=[C:17]([Cl:22])[CH:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)C.C(O)CO.[OH-].[K+]>O>[Cl:22][C:17]1[CH:16]=[C:15]([C:14]2[N:6]([CH2:5][C:4]([OH:3])=[O:24])[C:7]3=[N:8][CH:9]=[CH:10][CH:11]=[C:12]3[N:13]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 14390504HCID 14390504, compound

Product 1

HCID 156171932-(3,4-dichlorophenyl)3H-imidazo[4,5-b]pyridine-3-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-[3-[(3,4-dichlorobenzoyl)amino]-2-pyridinyl]glycine ethyl ester (33 g, 0.09 mole) and 167 ml of ethylene glycol was heated at reflux for 11/2 hr. After cooling, potassium hydroxide (8.4 g) in 40 ml of water was added and the reaction mixture was heated at reflux for 1 hr. The solution was filtered to remove yellow insoluble precipitate, the filtrate was diluted with 650 ml of water, and acidified with ethanolic hydrogen chloride. The solid, which formed, was collected by filtration, washed with water, and dried under high vacuum first at 50° C. overnight, then at 70° C. for 21/2 days to give 25.3 g (98%), mp 248°-49° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 11/2 hr
  3. temperatureAfter cooling
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 1 hr
  6. filtrationThe solution was filtered
  7. customto remove yellow insoluble precipitate
  8. additionthe filtrate was diluted with 650 ml of water
  9. customThe solid, which formed
  10. filtrationwas collected by filtration
  11. washwashed with water
  12. customdried under high vacuum first at 50° C. overnight
  13. customat 70° C. for 21/2 days to give 25.3 g (98%), mp 248°-49° C.

Sources & evidence

ORD record
ord-5138cb402e5641e7adf144aa6dc019fe
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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