Sodium Hydroxide → (5-Methyl-1H-imidazol-4-yl)(quinolin-7-yl)methanone

HRID 1643391Notes

Reaction equation

HRID 1643391 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:6]=1[C:7]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8].[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][C:2]1[NH:3][CH:4]=[N:5][C:6]=1[C:7]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66755765HCID 66755765, compound

Product 1

HCID 57965246(5-Methyl-1H-imidazol-4-yl)(quinolin-7-yl)methanone

Reagents, catalysts & solvents 1

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

Procedure

A solution of (8) in acetic acid/water (12 mL/8 mL) was heated at 110° C. for 1.5 h. The reaction was cooled to room temperature. Crushed ice was added, and basification of reaction with NaOH (s) to pH˜6 was followed. The aqueous layer was extracted with chloroform/isopropanol (3:1, 200 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered, and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 3% saturated ammonia methanol in dichloromethane to give (5-methyl-1H-imidazol-4-yl)(quinolin-7-yl)methanone (9) as a white solid (0.53 g, 2.24 mmol, 35% over 3 steps).

Workup

  1. additionCrushed ice was added
  2. extractionThe aqueous layer was extracted with chloroform/isopropanol (3:1, 200 mL)
  3. dry with materialThe pooled organic layers were dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customthe solvents were removed under vacuum
  6. customThe residue was purified by chromatography on silica gel with 3% saturated ammonia methanol in dichloromethane

Sources & evidence

ORD record
ord-cbae4f6faf7543488887f88093e5c72d
Source dataset
uspto-grants-2012_02
Patent number
US08119807B2

Reaction notes

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