Hydrochloric Acid → 6-(3-Phenylureido)nicotinic Acid

HRID 1878370Notes

Reaction equation

HRID 1878370 reaction equation
[C:1]1([NH:7][C:8](=[O:20])[NH:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].O.Cl>CO>[C:1]1([NH:7][C:8](=[O:20])[NH:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 57917619HCID 57917619, compound

Product 1

HCID 579176586-(3-Phenylureido)nicotinic AcidYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 6-(3-phenylureido)nicotinate (200 mg, 0.43 mmol) was dissolved in methanol (2 mL) at room temperature. Lithium hydroxide (100 mg, 4.17 mmol) was added, followed by water (10.5 mL). The mixture was heated to 50° C. and stirred overnight. The mixture was brought to pH 4-5 by addition of concentrated hydrochloric acid. The solid that had formed was then filtered and dried under vacuum to give the title compound (69 mg). MS (ESI) m/z 258.1[M+H]+

Workup

  1. customThe solid that had formed
  2. filtrationwas then filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-fa63a2b679e444d189986a95767fecc5
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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