P-Anisidine → HCID 178472672, compound

HRID 529472Notes

Reaction equation

HRID 529472 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[O-]S([O-])(=O)=O.[Na+].[Na+].O=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6](/[N:7]=[CH:18]\[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 24436Sodium SulfateHCID 70211Ethyl oxoacetate

Product 1

HCID 178472672HCID 178472672, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a round bottom flask was added 4-methoxyaniline (10 g, 81 mmol), toluene (100 mL) and Na2SO4 (40 gm). Then a solution of ethyl 2-oxoacetate (8.29 gm, 81 mmol) in toluene (20 mL) was slowly added to the reaction over 45 min. The reaction was stirred at rt for an additional 30 min. Then, the Na2SO4 was filtered off and the filtrate was concentrated to give (Z)-ethyl 2-(4-methoxyphenylimino)acetate (5.0 g, 24 mmol, 30% yield) as a clear oil.

Workup

  1. filtrationThen, the Na2SO4 was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-02e0496ae3414b44b6ca00fb61087554
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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