Ammonium Chloride → HCID 178477866, compound

HRID 1671294Notes

Reaction equation

HRID 1671294 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.CO[N:11](C)[C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+:22]>O1CCCC1.C([N-]C(C)C)(C)C.[Li+]>[Cl:1][C:2]1[N:3]=[C:4]2[NH:22][N:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]2=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 569575N-Methoxy-N-methylbenzamideHCID 6394372-Chloro-6-fluoropyridine

Product 1

HCID 178477866HCID 178477866, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724682Lithium diisopropylamideSolvent

Procedure

To a solution of 2-chloro-6-fluoropyridine (1.0 g, manufactured by Matrix Chemical LLC) in tetrahydrofuran (40 mL, manufactured by Kanto Chemical Co., Inc.), lithium diisopropylamide (23% solution in tetrahydrofuran/ethylbenzene/heptane, 5.07 mL, manufactured by Sigma-Aldrich Corp.) was added dropwise at −78° C., and the mixture was stirred for 30 minutes. Subsequently, N-methoxy-N-methylbenzamide (1.27 mL, manufactured by Sigma-Aldrich Corp.) was added thereto at the same temperature, and while the temperature was gradually raised to room temperature, the mixture was stirred overnight. A saturated aqueous solution of ammonium chloride (30 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (3×30 mL), washed with brine (30 mL), and dried (MgSO4). The solvent was then evaporated, and isopropanol (20 mL, manufactured by Kanto Chemical Co., Inc.) and hydrazine hydrate (1.22 mL, manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained residue. The mixture was heated and stirred for 12 hours at 80° C. The mixture was cooled to room temperature, and then hexane (10 mL) was added to the reaction solution. The solvent was evaporated, to give 180 mg of the title compound. LC-MS: HPLC retention time 1.53 minutes, m/z (M+H) 230, condition C-1.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  3. washwashed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was then evaporated
  6. additionisopropanol (20 mL, manufactured by Kanto Chemical Co., Inc.) and hydrazine hydrate (1.22 mL, manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained residue
  7. temperatureThe mixture was heated
  8. stirringstirred for 12 hours at 80° C
  9. temperatureThe mixture was cooled to room temperature
  10. additionhexane (10 mL) was added to the reaction solution
  11. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d80a6a90ae484e9ea52015f92660a31a
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

Loading…