Ethyl oxoacetate → Ethyl 2-((4-chloro-5-iodo-2-methoxyphenyl)amino)acetate

HRID 588775Notes

Reaction equation

HRID 588775 reaction equation
[Cl:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([NH2:9])=[C:4]([O:10][CH3:11])[CH:3]=1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=O.C([BH3-])#N.[Na+]>CO.CC(O)=O>[Cl:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([NH:9][CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

6

Reactant 3

HCID 70211Ethyl oxoacetateHCID 5003444Sodium cyanoborohydrideHCID 917583774-Chloro-5-iodo-2-methoxyaniline

Product 1

HCID 92135552Ethyl 2-((4-chloro-5-iodo-2-methoxyphenyl)amino)acetateYield 109.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-5-iodo-2-methoxybenzenamine (6 g, 21.2 mmol) in MeOH (50 mL) at room temperature, AcOH (3 drops) and ethyl glyoxalate (5.6 g, 27.5 mmol, 50% in toluene) were added. The mixture was stirred at room temperature for 2 h and then sodium cyanoborohydride (5.32 g, 84.8 mmol) was added to the mixture. The resulting mixture was stirred at 50° C. for 16 h. The mixture was allowed to cool to room temperature, and partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford the crude product (8.6 g).

Workup

  1. stirringThe resulting mixture was stirred at 50° C. for 16 h
  2. temperatureto cool to room temperature
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6df1f413d8344de7a3a6f817e8c34174
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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