Hydrochloric Acid → HCID 919484, compound

HRID 1945407Notes

Reaction equation

HRID 1945407 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:22])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21].Cl.C(OCC)(=O)C>C1COCC1.O.[Cl-].[Na+].O>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[O:13][CH2:12][C:11]([NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:23])=[O:2])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 1019273HCID 1019273, compound

Product 1

HCID 919484HCID 919484, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 21881883Oxolane--water (1/1)SolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid methyl ester (94.6 mg, 0.27 mmol) in THF/H2O (3:1, 25 mL) was treated with LiOHH2O (22.7 mg, 0.54 mmol) at room temperature. The reaction mixture was then acidified with 10% HCl to PH 2, and added ethyl acetate and brine. The organic phase was washed with water, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=6:1) to give 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid as a white solid (81.7 mg, 88.9% yield).

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried (MgSO4 anh)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=6:1)

Sources & evidence

ORD record
ord-89579b7dd6b448b7a72a681d600e7bbc
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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