Hydrochloric Acid → HCID 22344491, compound

HRID 505570Notes

Reaction equation

HRID 505570 reaction equation
Cl.[C:2]([O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2)(=[O:4])[CH3:3]>CCO.O=[Pt]=O>[C:2]([O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][NH:11]2)(=[O:4])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22344493HCID 22344493, compound

Product 1

HCID 22344491HCID 22344491, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

In accordance with J. Org. Chem. 1978, 43 (10), 1975-1980, PtO2 (120 mg, 1.06 mmol) and concentrated HCl (20 μL) were added to a solution of quinolin-5-yl acetate (1.0 g, 5.34 mmol) in EtOH (30 mL) and the mixture was purged with N2 followed by H2. The mixture was then stirred at room temperature for 48 hours, at which point the starting material had been consumed as determined by LC-MS. The reaction mixture was then filtered through celite, and washed with MeOH, chloroform, and a small amount of TEA. The filtrate was concentrated under reduced pressure, and the resulting residue was purified on a silica gel column (10% to 80% EtOAc/hexanes) to afford the title product. LRMS (M+1)=192.3

Workup

  1. customthe mixture was purged with N2
  2. customhad been consumed
  3. filtrationThe reaction mixture was then filtered through celite
  4. washwashed with MeOH, chloroform
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified on a silica gel column (10% to 80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b636e36698964c64a38331a4556009a5
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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