Hydrochloric Acid → HCID 117610599, compound

HRID 588769Notes

Reaction equation

HRID 588769 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][CH2:10][C:11]([O:13]CC)=[O:12])=[C:4]([OH:16])[CH:3]=1.O1CCCC1.O[Li].O.Cl>O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[C:4]([OH:16])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 117610965Ethyl 2-(4,5-dichloro-2-hydroxyphenylamino)acetate

Product 1

HCID 117610599HCID 117610599, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-((4,5-dichloro-2-hydroxyphenyl)amino)acetate (2 g, 7.6 mmol) in of 4:1 mixture of tetrahydrofuran and water (30 mL) at room temperature, LiOH.H2O (3.2 g, 76 mmol) were added and the resulting mixture was stirred for 30 min and then acidified with aqueous HCl (1N) to adjust the pH to 3-5. The mixture was extracted with ethyl acetate (40 mL×3). The combined organic layer was washed with brine (40 mL×3), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the crude product (2 g) which was used directly in the next step without further purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (40 mL×3)
  2. washThe combined organic layer was washed with brine (40 mL×3)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37edc36115b947c481bdec83ebf19cca
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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