Ammonium Chloride → HCID 131723398, compound

HRID 1370016Notes

Reaction equation

HRID 1370016 reaction equation
I[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH:14]([Mg]Br)=[CH2:15].[Li+].CCC[CH2-].[C:23]([O:30]C(OC(C)(C)C)=O)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].[Cl-].[NH4+]>C1COCC1.CC(OC)(C)C>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:11]([CH:12]([OH:13])[CH:14]=[CH2:15])[CH:2]=1.[C:26]([O:25][C:23](=[O:24])[O-:30])([CH3:29])([CH3:28])[CH3:27]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 61028n-Butyl lithiumHCID 90495Di-tert-butyl dicarbonateHCID 109897002-Iodoquinoline-3-carbaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 131723398HCID 131723398, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 2-iodo-3-quinoline carboxaldehyde (3 g, 10.6 mmol) in THF (25 ml) at −5° C., vinylmagnesium bromide (1 M solution, 10.8 ml, 10.8 mmol) was added. It was stirred at that temperature until the starting material disappears, which takes about one hour. N-butyllithium (8.5 ml, 2.5 M soln, 21.2 mmol) was added and the solution was stirred for another 25 min and then quenched with t-butanol (1.63 g, 22 mmol, only the C-2 anion is being quenched). Then a solution of di-tert-butyl dicarbonate (2.54 g, 11.6 mmol) was added and the solution was stirred for 2 h at −5° C. The reaction was then worked up with MTBE (60 ml) and 10% ammonium chloride solution (25 ml). The organic layer washed again with saturated NaCl solution and it was concentrated to an orange oil which crystallised on standing at 0° C. overnight. It was used as such for alkylation experiments. Yield=2.8 g (92.7%)

Workup

  1. stirringthe solution was stirred for another 25 min
  2. customquenched with t-butanol (1.63 g, 22 mmol
  3. customonly the C-2 anion is being quenched)
  4. stirringthe solution was stirred for 2 h at −5° C
  5. washThe organic layer washed again with saturated NaCl solution and it
  6. concentrationwas concentrated to an orange oil which
  7. customcrystallised
  8. waiton standing at 0° C. overnight

Sources & evidence

ORD record
ord-b5bfa501923d4ccfa06d3a93fbb43e2b
Source dataset
uspto-grants-2003_06
Patent number
US06579986B2

Reaction notes

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