Hydrochloric Acid → HCID 86619498, compound

HRID 1170188Notes

Reaction equation

HRID 1170188 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13]([C:17]#[N:18])=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([Mg]Br)=[CH:26][CH:25]=1.Cl.[OH-].[Na+]>C(OCC)C.C1COCC1>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:17](=[NH:18])[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:14]=2[CH:15]=[CH:16][C:7]([NH:6][CH2:5][C:4]2[CH:19]=[CH:20][CH:21]=[CH:22][C:3]=2[O:2][CH3:1])=[N:8]3)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67332820HCID 67332820, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 86619498HCID 86619498, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (ice bath) and stirred suspension of 2-(2-methoxy-benzylamino)-quinoline-5-carbonitrile (289 mg, 1.0 mmol) in diethylether (3 ml) and THF (1 ml) was added drop wise a 1M solution of 4-fluorophenyl-magnesium bromide (4 ml, 4.0 mmol), the reaction mixture was heated under reflux conditions for 24 h and poured into ice-water (15 ml). 2N HCl (5 ml) was added, the mixture was stirred at room temperature for 10 min, 3 N NaOH (5 ml) was added and the mixture was extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with brine (2×20 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/hexane) to yield the title compound as white solid (159 mg, 41%).

Workup

  1. temperatureTo a cooled (ice bath)
  2. temperaturethe reaction mixture was heated under reflux conditions for 24 h
  3. stirringthe mixture was stirred at room temperature for 10 min
  4. extractionthe mixture was extracted with ethyl acetate (2×40 ml)
  5. washThe combined organic layers were washed with brine (2×20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/hexane)

Sources & evidence

ORD record
ord-b2bf1dc03d3949fc88dd0a99fc7cc379
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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