Potassium Hydroxide → HCID 131715722, compound

HRID 1709464Notes

Reaction equation

HRID 1709464 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][NH:6][C:7](=[O:25])[CH2:8][N:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=[C:10]1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)C.[OH-].[K+:28]>C(O)C>[OH2:3].[K+:28].[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:10]2[N:9]([CH2:8][C:7]([NH:6][CH2:5][C:4]([O-:26])=[O:3])=[O:25])[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14390235HCID 14390235, compound

Product 1

HCID 131715722HCID 131715722, compoundYield 115.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[[2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridin-3-yl]acetyl]glycine ethyl ester (4.0 g, 0.0108 mole), potassium hydroxide (0.62 g, 0.011 mole), and 100 ml of 95% ethyl alcohol was heated at reflux for 2 hrs. The hot solution was filtered and allowed to cool to initiate crystallization. The solid was diluted with 95% ethyl alcohol, filtered, and washed with a little 95% ethyl alcohol. The solid was dried under high vacuum at room temperature overnight to give 2.5 g (55%) of title compound, m.p. >300° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hrs
  3. filtrationThe hot solution was filtered
  4. temperatureto cool
  5. customcrystallization
  6. additionThe solid was diluted with 95% ethyl alcohol
  7. filtrationfiltered
  8. washwashed with a little 95% ethyl alcohol
  9. customThe solid was dried under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-13dd6ddcf7cb42878b5240bdb1296038
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

Loading…