Phenylacetyl chloride → HCID 54286782, compound

HRID 2392706Notes

Reaction equation

HRID 2392706 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:19]1([CH2:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[C:19]1([CH2:25][C:26]([NH:1][C:2]2[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=2)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chloride2×HCID 8471Triethylamine2×HCID 9898880Methyl 3-aminopicolinate

Product 1

HCID 54286782HCID 54286782, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dry CH2Cl2 (20 mL) was added to methyl 3-aminopicolinate (116) (0.421 g, 2.77 mmol). The solution was purged with nitrogen. Triethyl amine (1.16 mL, d=0.726, 8.31 mmol) was added to the solution via syringe. Phenylacetyl chloride (117) (0.805 mL, d=1.169, 6.09 mmol) was added to the solution via syringe. The mixture was stirred overnight at room temperature under nitrogen. The mixture was then stirred at 40° C. for 6 h. More triethyl amine (0.50 mL, 3.6 mmol) was added and, an hour later, more phenylacetyl chloride (0.400 mL, 3.02 mmol) was added. The mixture was stirred an additional hour and allowed to cool to room temperature. The reaction was quenched with water (20 mL), and the aqueous layer removed. The organic layer washed with water (3×15 mL), and dried with MgSO4. Silica gel was added and the slurry rota-evaporated to dryness. The resulting silica was chromatographed on silica (40 g, Davisil, grade 643, mesh 200-450) and eluded with EtOAc-hexanes (2:1, 400 mL). The appropriate fractions were collected (Rf =0.35). The solvent was rota-evaporated to yield the title compound (118) as a yellow oil, which, upon drying, precipitated out as a yellow solid (0.4463 g, 59.6%); Rf =0.35. 1H NMR (CDCl3) δ3.78 (s, 2, benzyllic), 3.97 (s, 3, CH3O--), 7.38 (m, 6, phenyl & H-5), 8.39, (dd, J1 =0.6, J2 =3.9, 1, H-4), 9.10 (dd, J1 =8.4, J2 =8.3, 1, H-6), 10.96 (s, 1, NH); MS (m./z) 270 (M+, 35), 211 (35), 179 (85), 153 (40), 147 (65), 119 (40), 94, (40), 91 (100).

Workup

  1. customThe solution was purged with nitrogen
  2. stirringThe mixture was then stirred at 40° C. for 6 h
  3. stirringThe mixture was stirred an additional hour
  4. temperatureto cool to room temperature
  5. customThe reaction was quenched with water (20 mL)
  6. customthe aqueous layer removed
  7. washThe organic layer washed with water (3×15 mL)
  8. dry with materialdried with MgSO4
  9. additionSilica gel was added
  10. customthe slurry rota-evaporated to dryness
  11. customThe resulting silica was chromatographed on silica (40 g, Davisil, grade 643, mesh 200-450)
  12. customThe appropriate fractions were collected (Rf =0.35)
  13. customThe solvent was rota-evaporated

Sources & evidence

ORD record
ord-e18455154d584312a03671be4108cb83
Source dataset
uspto-grants-1998_09
Patent number
US05801183

Reaction notes

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