Lithium hydroxide, monohydrate → N-(4-Chloro-5-iodo-2-methoxyphenyl)glycine

HRID 588776Notes

Reaction equation

HRID 588776 reaction equation
[Cl:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([NH:9][CH2:10][C:11]([O:13]CC)=[O:12])=[C:4]([O:16][CH3:17])[CH:3]=1.O[Li].O>C1COCC1.O>[Cl:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[C:4]([O:16][CH3:17])[CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 92135552Ethyl 2-((4-chloro-5-iodo-2-methoxyphenyl)amino)acetate

Product 1

HCID 92135553N-(4-Chloro-5-iodo-2-methoxyphenyl)glycineYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-chloro-5-iodo-2-methoxyphenylamino)acetate (8.6 g, 22.9 mmol) in THF (50 mL) and water (50 mL), LiOH.H2O (1.96 g, 45.9 mmol) was added and the resulting mixture was stirred at room temperature for 2 h. The mixture was washed with 20% ethyl acetate/petroleum ether. The aqueous layer was acidified with aqueous HCl (1 M) to adjust PH to 3-4 and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product (5 g, 64% yield).

Workup

  1. washThe mixture was washed with 20% ethyl acetate/petroleum ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f7fd28ddc564a4198a726429568e0c1
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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