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Citric Acid → 5-(4-Chloro-phenyl)-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinic acid

HRID 1159275
Notes
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Reaction equation

HRID 1159275 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[C:7]([O:17][CH2:18][C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)=[N:6][CH:5]=1.O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[C:7]([O:17][CH2:18][C:19]3[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=3)=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([OH:25])=[O:2])=[CH:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 675050775-(4-Chloro-phenyl)-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinic acid methyl ester

Product 1

HCID 675046735-(4-Chloro-phenyl)-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinic acid

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
80 °C

Procedure

5-(4-Chloro-phenyl)-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinic acid methyl ester (0.28 g, 0.8 mmol) was dissolved in tetrahydrofuran (4.5 mL). Water (1.5 mL) and lithium hydroxide (99 mg, 2.3 mmol) was added and the mixture was stirred for 1 h at 80° C. The mixture was cooled to room temperature; citric acid (4 mL, 10%) was added and the mixture was extracted with ethyl acetate. Organic phases were pooled dried with Na2SO4 and the solvent evaporated to give a quantitative yield of the title compound as beige solid, MS (ISP) 342.0 (M−H)−.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialOrganic phases were pooled dried with Na2SO4
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-1db3a1fc47c64825a2865557a69bc69d
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07812028B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes