Methanol → HCID 66696224, compound

HRID 1396661Notes

Reaction equation

HRID 1396661 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:13]=[C:12]([N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[CH:19]2[CH2:23][CH2:22][O:21][CH2:20]2)[C:11]([N+:24]([O-])=O)=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[Cl-].[NH4+].O1CCCC1.CO>O>[NH2:24][C:11]1[C:12]([N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[CH:19]2[CH2:23][CH2:22][O:21][CH2:20]2)=[CH:13][C:4]([CH2:3][O:2][CH3:1])=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86701153HCID 86701153, compound

Product 1

HCID 66696224HCID 66696224, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 6.65 g of methyl 2-(methoxymethyl)-5-nitro-4-[2-(tetrahydrofuran-3-yl)-1H-imidazol-1-yl]benzoate, 980 mg of ammonium chloride, 33.0 mL of tetrahydrofuran, 66.0 mL of methanol, and 33.0 mL of water was added 4.8 g of reduced iron, followed by stirring at 70° C. for 4.5 hours. The insoluble matter was filtered through celite. The filtrate was concentrated, and water and ethyl acetate were added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 5.30 g of methyl 5-amino-2-(methoxymethyl)-4-[2-(tetrahydrofuran-3-yl)-1H-imidazol-1-yl]benzoate as a brown solid.

Workup

  1. filtrationThe insoluble matter was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. additionwater and ethyl acetate were added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-aab383657729478fb4a6a013895fbf10
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

Loading…