Acetic Acid → HCID 22501659, compound

HRID 1813878Notes

Reaction equation

HRID 1813878 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:21])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19]C)=[O:18])=[CH:12][CH:11]=1.[OH-].[Na+].Cl.C(O)(=O)C>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:21])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22501663HCID 22501663, compound

Product 1

HCID 22501659HCID 22501659, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-(2-pyridylureido)phenylacetate (5.7 g, 20.0 mmol) in methanol (20 mL) was treated with 1 N NaOH (40 mL). The reaction was stirred for 16 h, then acidified carefully with 1 N HCl to pH 7 then with acetic acid to pH 3. The product was filtered and washed with methanol then ether to give 4-(2-pyridyl)ureidophenylacetic acid (4.7 g, 87%) as a white powder: 1H NMR (CD3SOCD3, 300 MHz, ppm) 10.62 (bs, 1H), 9.53 (bs, 1H), 8.39 (d, 1H), 7.82 (t, 1H), 7.63-7.55 (m, 1H), 7.33-7.27 (d, 2H), 7.14-7.08 (m, 1H), 3.62 (s, 3H).

Workup

  1. filtrationThe product was filtered
  2. washwashed with methanol

Sources & evidence

ORD record
ord-37389fb78f37471d9f67fcfa0b6e71e0
Source dataset
uspto-grants-2005_04
Patent number
US06875743B1

Reaction notes

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