Methanol → HCID 72262876, compound

HRID 78108Notes

Reaction equation

HRID 78108 reaction equation
[N+:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][N:7]=1)([O-])=[O:2].CO.C[O-].[Li+].C(=O)(O)[O-].[Na+].C(Cl)[Cl:30]>[Ti](Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[O:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([Cl:30])=[N:1][OH:2])=[N:7][CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 4177230Lithium methanolateHCID 57626337HCID 57626337, compound

Product 1

HCID 72262876HCID 72262876, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 2-(2-nitro-ethyl)-5-phenoxy-pyridine (76 mg, 0.31 mmol) described in Manufacturing Example 121-1-4 and methanol (6.0 mL) was added lithium methoxide (24 mg, 0.62 mmol) at room temperature, which was stirred for 3 minutes, and then the solvent was evaporated under a reduced pressure. Methylene chloride (10 mL) was added to the residue, titanium(IV) chloride (0.11 mL, 1.0 mmol) was added at room temperature, which was stirred for 10 minutes. Cold aqueous sodium bicarbonate and ethyl acetate were added to the reaction solution, which was filtered through a Celite pad, and then the organic layer was separated. The organic layer was concentrated under a reduced pressure to obtain the title compound (56 mg, 69%).

Workup

  1. customthe solvent was evaporated under a reduced pressure
  2. additionwas added at room temperature
  3. stirringwhich was stirred for 10 minutes
  4. filtrationwas filtered through a Celite pad
  5. customthe organic layer was separated
  6. concentrationThe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-f31e2e74ffd048c09f0b7a4071eb6334
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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