Hydrochloric Acid → HCID 24991561, compound

HRID 1170189Notes

Reaction equation

HRID 1170189 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=N)[C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])=[N:14]3)=[CH:4][CH:3]=1.Cl.C([O-])(O)=[O:32].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])=[N:14]3)=[O:32])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86619498HCID 86619498, compound

Product 1

HCID 24991561HCID 24991561, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {5-[(4-fluoro-phenyl)-imino-methyl]-quinolin-2-yl}-(2-methoxy-benzyl)-amine (130 mg, 0.34 mmol), 2N HCl (4 ml) and THF (1 ml) was stirred at room temperature for 23 h, poured into saturated NaHCO3 solution (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel to yield the title compound as light yellow gum (115 mg, 88%).

Workup

  1. extractionextracted with ethyl acetate (2×30 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel

Sources & evidence

ORD record
ord-458a188ab82d467db7625b4deaf63448
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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