Ethyl Acetate → HCID 18371289, compound

HRID 2301211Notes

Reaction equation

HRID 2301211 reaction equation
Cl[C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].[C:13]1(OB(O)O)[CH:18]=[CH:17]C=[CH:15][CH:14]=1.[C:23](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:7][C:6]1[CH:8]=[C:2]([CH3:23])[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]=1[C:9]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 837726-Chloro-4-nitro-o-toluidine

Product 1

HCID 18371289HCID 18371289, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

1.87 g (0.01 mole) of 5-chloro-2-methyl-4-nitroaniline and 0.013 mole of phenylboric acid were dissolved in 70 mL of 1,2-dimethoxyethane under argon. Then, 0.5 g (0.0005 mole) of tetrakis(triphenylphosphine)palladium and 13 mL of 2 N potassium carbonate solution were added, and the reaction mixture was heated to 80° C. At the end of the reaction, the reaction mixture was poured into 100 mL of ethyl acetate. The organic phase was extracted with dilute sodium hydroxide solution and then dried over magnesium sulfate. The solvent was distilled off from a rotary evaporator, and the residue was purified [by column chromatography] on silica gel using hexane/ethyl acetate (8:1) [as the eluent].

Workup

  1. customAt the end of the reaction
  2. extractionThe organic phase was extracted with dilute sodium hydroxide solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off from a rotary evaporator
  5. customthe residue was purified [by column chromatography] on silica gel

Sources & evidence

ORD record
ord-758aff454fc346bfabdabb325d65d989
Source dataset
uspto-grants-2002_12
Patent number
US06500213B1

Reaction notes

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