HCID 14639165, compound → HCID 14639176, compound

HRID 1460142Notes

Reaction equation

HRID 1460142 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]1[N:16]([C:20]([C:22]2[C:23](Cl)=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:21])[CH2:17][CH2:18][N:19]=1>C(O)(C)(C)C>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:23]2[N:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:20](=[O:21])[N:16]2[CH2:17][CH2:18][NH:19][C:15]=12

Participants

4

Reactant 2

HCID 14639165HCID 14639165, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14639176HCID 14639176, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Add potassium tert.-butoxide (0.928g) to 2-[(2-chlorophenyl)methyl]-1-[(2-chloro-3-pyridinyl)carbonyl]-4,5-dihydro-1H-imidazole (2.57g) suspended in tert.-butanol (25 ml). Reflux the reaction mixture under nitrogen for 5 hours, cool the resulting suspension, and evaporate the solvent Partition the residue between chloroform and water, separate and dry the chloroform solution over sodium sulfate. Filter the dried solution, evaporate the solvent, and crystallize the residue from methanol to give 10-(2-chlorophenyl)-2,3-dihydro-imidazo [1,2-g][1,6]naphthyridin-5(1H)-one, mp 295°-297° C. (d).

Workup

  1. temperatureReflux the reaction mixture under nitrogen for 5 hours
  2. temperaturecool the resulting suspension
  3. customevaporate the solvent
  4. customPartition the residue between chloroform and water
  5. customseparate
  6. dry with materialdry the chloroform solution over sodium sulfate
  7. filtrationFilter the dried solution
  8. customevaporate the solvent
  9. customcrystallize the residue from methanol

Sources & evidence

ORD record
ord-d4da32babd6e45b3afa169a707aeb48c
Source dataset
uspto-grants-1991_12
Patent number
US05070086

Reaction notes

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