Methyl iodide → 6-Nitro-o-anisidine

HRID 275786Notes

Reaction equation

HRID 275786 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:13].I[CH3:15]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O.O1CCCC1>[NH2:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[O:13][CH3:15]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 854916-Nitro-o-anisidine

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium iodide (0.4 g), sodium hydroxide (4.0 g) in water (40 ml) and iodomethane (3.4 ml) were added to 2-amino-3-nitrophenol (4.0 g) dissolved in tetrahydrofuran (80 ml) at ambient temperature. This mixture was stirred overnight then concentrated in vacuo. After pouring into water (200 ml) it was extracted into ethyl acetate (2×200 ml) then washed with aqueous sodium bicarbonate (100 ml) and saturated brine (100 ml). The solution was dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo to afford the title compound as a dark solid (4.4 g).

Workup

  1. concentrationthen concentrated in vacuo
  2. additionAfter pouring into water (200 ml) it
  3. extractionwas extracted into ethyl acetate (2×200 ml)
  4. washthen washed with aqueous sodium bicarbonate (100 ml) and saturated brine (100 ml)
  5. dry with materialThe solution was dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-faf4e9c08a874048924c730439fd7f29
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Reaction notes

Loading…