Potassium Hydroxide → HCID 20062746, compound

HRID 1084810Notes

Reaction equation

HRID 1084810 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[CH2:4][CH2:3]1.[CH3:13][C:14]1[N:18](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=[N:16][C:15]=1[CH:38]=O.[OH-].[K+]>CO>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]([CH2:38][C:15]2[N:16]=[CH:17][NH:18][C:14]=2[CH3:13])=[CH:3]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 4204192,3-Dihydro-1-methyl-4(1H)-quinolinoneHCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 20062746HCID 20062746, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of 2,3-dihydro-1-methyl-4(1H)-quinolinone (915 mg) and 5-methyl-1-(triphenylmethyl)-1H-imidazole-4-carboxaldehyde (2.0 g) in methanol (25 ml) was treated with a solution of potassium hydroxide (0.5 g) in methanol (5 ml). The suspension was stirred at room temperature for 44 h and then filtered. The collected solid was heated at reflux in a mixture of acetic acid (6 ml), water (5 ml) and THF (15 ml) for 3 h. The solution was treated cautiously with 8% aqueous sodium bicarbonate (180 ml) and extracted with dichloromethane (3×60 ml). The combined, dried organic extracts were evaporated to give a solid, which was purified by FCC eluting with System A (100:12:1.2) to give the title compound (208 mg), m.p. 110°-113°.

Workup

  1. filtrationfiltered
  2. temperatureThe collected solid was heated
  3. temperatureat reflux in a mixture of acetic acid (6 ml), water (5 ml) and THF (15 ml) for 3 h
  4. additionThe solution was treated cautiously with 8% aqueous sodium bicarbonate (180 ml)
  5. extractionextracted with dichloromethane (3×60 ml)
  6. customdried organic extracts were evaporated
  7. customto give a solid, which
  8. customwas purified by FCC
  9. washeluting with System A (100:12:1.2)

Sources & evidence

ORD record
ord-395d81e90dfa42a3830fd2a2f544f324
Source dataset
uspto-grants-1991_04
Patent number
US05006544

Reaction notes

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