Hydrochloric Acid → 3-[N'-(2-bromophenyl)ureido]-2-methoxy-6-pyridylacetic acid

HRID 354345Notes

Reaction equation

HRID 354345 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:25])[NH:10][C:11]1[C:12]([O:23][CH3:24])=[N:13][C:14]([CH2:17][C:18]([O:20]CC)=[O:19])=[CH:15][CH:16]=1.[OH-].[Na+].Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:25])[NH:10][C:11]1[C:12]([O:23][CH3:24])=[N:13][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69333268ethyl 3-[N'-(2-bromophenyl)ureido]-2-methoxy-6-pyridylacetate

Product 1

HCID 693333973-[N'-(2-bromophenyl)ureido]-2-methoxy-6-pyridylacetic acidYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[N′-(2-bromophenyl)ureido]-2-methoxy-6-pyridylacetate (2.90 g, 7.10 mmol), 0.25 N NaOH (56.8 ml, 14.2 mmol), and THF (50 ml) was stirred for 5 h. The mixture was neutralized with 1 N HCl and the resulting precipitate was collected by filtration. The residue was recrystallized from CHCl3—MeOH-hexane to give 3-[N′-(2-bromophenyl)ureido]-2-methoxy-6-pyridylacetic acid (2.40 g, 89%) as a colorless crystalline powder. mp 195-197 IC; 1H-NMR (DMSO-d6), δ3.59 (s, 2 H), 3.95 (s, 3 H), 6.88 (d, J=8.1 Hz, 1 H), 6.97-7.01 (m, 1 H), 7.33 (t, J=7.3 Hz, 1 H), 7.61 (d, J=8.1 Hz, 1 H), 7.95-7.97 (m, 1 H), 8.29 (d, J=8.1 Hz, 1 H), 8.81 (s, 1 H), 9.10 (s, 1 H), 12.35 (br s, 1 H); Anal. Calcd. for C15H14BrN3O4: C, 47.39; H, 3.71; N, 11.05. Found: C, 47.27; H, 3.59; N, 10.86.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customThe residue was recrystallized from CHCl3—MeOH-hexane

Sources & evidence

ORD record
ord-5937e78ec5314ec5ab617456e01820ab
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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