Methanol → HCID 72262876, compound

HRID 1691214Notes

Reaction equation

HRID 1691214 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-601760943cf84428a48609607a249367
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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