Ammonium Chloride → HCID 178487492, compound

HRID 392581

Reaction equation

HRID 392581 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]=2)=[O:7])[N:3]=[CH:2]1.[CH:20]([Mg]Cl)([CH3:22])[CH3:21].[Cl-].[NH4+]>C1COCC1.O>[NH:1]1[CH:5]=[C:4]([C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]=2)([OH:7])[CH:20]([CH3:22])[CH3:21])[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 178418918HCID 178418918, compoundHCID 178487490HCID 178487490, compound

Product 1

HCID 178487492HCID 178487492, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

(1H-Imidazol-4-yl)-(6-methoxynaphthalen-2-yl)ketone (6.50 g) was dissolved in THF (120 ml) and the mixture was cooled to −10° C. A solution (2.0 M; 38.7 ml) of isopropyl magnesium chloride in THF was slowly added dropwise and the mixture was stirred for 30 min. To the reaction mixture was added saturated aqueous solution of ammonium chloride and the mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine, and after drying, concentrated. The obtained residue was purified by silica gel column chromatography (eluate, chloroform:methanol=20:1→10:1) and recrystallized from ethyl acetate to give the title compound (5.04 g) as a colorless crystalline powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customafter drying
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (eluate, chloroform:methanol=20:1→10:1)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-26c6fc93a0014f97bc37693d9637e63e
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Linked notes

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