Sodium Hydroxide → HCID 178519869, compound

HRID 747279Notes

Reaction equation

HRID 747279 reaction equation
[N:1]1[C:10]2[C:5](=[C:6]([C:11]([C:13]3[N:14]=[CH:15][N:16](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:17]=3)=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)(=O)C.O>[NH:16]1[CH:17]=[C:13]([C:11]([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]=[CH:3][CH:2]=[N:1]3)=[O:12])[N:14]=[CH:15]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59749548HCID 59749548, compound

Product 1

HCID 178519869HCID 178519869, compound

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

Quinolin-5-yl-(1-trityl-1H-imidazol-4-yl)-methanone (Intermediate G1) in acetic acid:water (˜2:1) was heated to 100° C. for 1 h. The mixture was basified with 1 M NaOH and extracted (6×) with CHCl3:iPrOH (3:1). The organic solution was dried over MgSO4, filtered, and concentrated onto silica gel. The material was eluted from a column of silica with 5% NH3-MeOH:CH2Cl2 to give (1H-imidazol-4-yl)-quinolin-5-yl-methanone (Intermediate G2).

Workup

  1. extractionextracted (6×) with CHCl3:iPrOH (3:1)
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated onto silica gel
  5. washThe material was eluted from a column of silica with 5% NH3-MeOH

Sources & evidence

ORD record
ord-8803bd4236ce47f6afadc3a28c88aa0b
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

Loading…