Hydrochloric Acid → 4-{[(2,4-Dichlorophenoxy)acetyl]amino}benzoic acid

HRID 1945408Notes

Reaction equation

HRID 1945408 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:22])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:5]=1.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:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:23])=[O:2])=[CH:5][CH:6]=1)=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4572426Methyl 4-{[(2,4-dichlorophenoxy)acetyl]amino}benzoate

Product 1

HCID 6681384-{[(2,4-Dichlorophenoxy)acetyl]amino}benzoic acidYield 70.6%

Reagents, catalysts & solvents 2

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

Procedure

4-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid methyl ester (127.7 mg, 0.36 mmol) in THF/H2O (3:1, 9 mL) was treated with LiOHH2O (30.2 mg, 0.72 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=4:1) to give 4-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid as a white solid (86.4 mg, 70.6% 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=4:1)

Sources & evidence

ORD record
ord-1f95f7ae860348f5a486719cec0b3d3e
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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