Water → Methyl {2-chloro-4-[(4,6-dimethyl-3-nitro-2-pyridinyl)amino]phenyl}acetate

HRID 724149Notes

Reaction equation

HRID 724149 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:4]([Cl:13])[CH:3]=1.Cl[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[C:19]([CH3:24])[CH:18]=[C:17]([CH3:25])[N:16]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[Cl:13][C:4]1[CH:3]=[C:2]([NH:1][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[C:19]([CH3:24])[CH:18]=[C:17]([CH3:25])[N:16]=2)[CH:7]=[CH:6][C:5]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 218755782-Chloro-4,6-dimethyl-3-nitropyridineHCID 21876454Methyl 2-(4-amino-2-chlorophenyl)acetate

Product 1

HCID 86611502Methyl {2-chloro-4-[(4,6-dimethyl-3-nitro-2-pyridinyl)amino]phenyl}acetateYield 30.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl 2-(4-amino-2-chlorophenyl)acetate (step 4, 2.6 g, 13.0 mmol) and 4,6-Dimethyl-3-nitro-2-pyridine (step 2 of Example 1, 2.4 g, 13.0 mmol) in DMSO was added diisopropylethylamine. The resulting mixture was stirred for 9 h at 50° C. To the mixture was poured into water and extracted with ethyl acetate (3×30 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give a brown oil. This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1) to give 1.4 g (29%) of title compound as yellow solid.

Workup

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a brown oil
  6. customThis was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-4f6ee530328a4bbd94e162551aa98a02
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

Loading…