4-Fluoro-2-methylaniline → HCID 68602196, compound

HRID 1993339Notes

Reaction equation

HRID 1993339 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=O.[F:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([CH3:16])[CH:10]=1>C1(C)C=CC=CC=1>[CH2:6]([O:5][C:1](=[O:4])[CH:2]=[N:13][C:12]1[CH:14]=[CH:15][C:9]([F:8])=[CH:10][C:11]=1[CH3:16])[CH3:7]

Participants

4

Reactant 2

HCID 679824-Fluoro-2-methylanilineHCID 70211Ethyl oxoacetate

Product 1

HCID 68602196HCID 68602196, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of ethyl glyoxalate (50% solution in toluene-40.8 mL) in toluene (180 mL) was heated to reflux for 1.5 hours under a Nitrogen atmosphere, in a flask equipped with a Dean Stark apparatus. Then, a solution of 4-fluoro-2-methyl-aniline (10 g) in dry toluene (20 mL) was slowly added. The mixture was heated to reflux for 3 hours, then it was concentrated in vacuo. The residue was purified by flash chromatography (toluene/CH/AcOEt 4:4:2) to give the title compound (13.06 g) as a yellow oil.

Workup

  1. temperatureto reflux for 1.5 hours under a Nitrogen atmosphere, in a flask
  2. customequipped with a Dean Stark apparatus
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 3 hours
  5. concentrationit was concentrated in vacuo
  6. customThe residue was purified by flash chromatography (toluene/CH/AcOEt 4:4:2)

Sources & evidence

ORD record
ord-70d77476a6e3496c880b2bfc112e341f
Source dataset
uspto-grants-2010_01
Patent number
US07652012B2

Reaction notes

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