Hydrochloric Acid → HCID 89906543, compound

HRID 526691Notes

Reaction equation

HRID 526691 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:8]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[N:7][C:6]=1[CH3:28])C.[Li+].[OH-].Cl>C1COCC1.O>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]2[C:8]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:20][CH:19]=3)=[N:7][C:6]([CH3:28])=[C:5]([CH:10]=2)[C:4]([OH:29])=[O:3])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89907317HCID 89907317, compound

Product 1

HCID 89906543HCID 89906543, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.6 g of 5-(4-Chloro-phenyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester and 136 mg of LiOH in 5 ml of THF and 5 ml of water was stirred at room temperature for 16 h. After 16 h, the mixture was brought to pH 2 by addition of 1 M hydrochloric acid. The reaction mixture was concentrated under reduced pressure and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. The residue was codistilled twice with dichloromethane and twice with toluene The isolated crude product was used in the next reaction step. Yield: 1.6 g.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customisolated crude product
  6. customwas used in the next reaction step

Sources & evidence

ORD record
ord-704d58b3692d40f9bf7d48c6d281792a
Source dataset
uspto-grants-2016_05
Patent number
US09346757B2

Reaction notes

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