2-Iodotoluene → N-acetyl-o-toluidine

HRID 984693

Reaction equation

HRID 984693 reaction equation
[F-].[K+].CNCCNC.I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].[CH3:17]/[C:18](/[O:24][Si](C)(C)C)=[N:19]\[Si](C)(C)C>[Cu]I.C1(C)C=CC=CC=1>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:19][C:18](=[O:24])[CH3:17]

Participants

7

Reactant 4

HCID 51282-IodotolueneHCID 8070N,N'-DimethylethylenediamineHCID 522689Potassium FluorideHCID 6913588N,O-bis(trimethylsilyl)acetamide

Product 1

HCID 8443N-acetyl-o-toluidineYield 52%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), KF (350 mg, 6.0 mmol), evacuated, backfilled with Ar. N,N′-Dimethylethylenediamine (11 μL, 0.10 mmol, 10 mol %), 2-iodotoluene (128 μL, 1.01 mmol), N,O-bis(trimethylsilyl)acetamide (300 μL, 1.21 mmol), and toluene (1.0 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 16 h. The resulting suspension was allowed to reach room temperature and then filtered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate (20 mL). The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 1:4; 15 mL fractions). Fractions 10-17 provided 78 mg (52% yield) of N-(2-methylphenyl)acetamide as white needles.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate (20 mL)
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 1:4; 15 mL fractions)

Sources & evidence

ORD record
ord-6fed5fec8902484fbd9c1448f51a015e
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Linked notes

Loading…