Lithium hydroxide, monohydrate → 5-Cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid

HRID 631952

Reaction equation

HRID 631952 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH2:12]2)=[C:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[N:6]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O>[CH:11]1([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=2[NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 710873965-Cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 710872815-Cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acidYield 10.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid methyl ester (62 mg, 184 μmol) and lithium hydroxide hydrate (9.3 mg, 221 μmol) in THF (100 μl) and water (50 μl) was stirred at ambient temperature for 20 h. The reaction mixture was poured onto 1 M HCl/ice water (1×20 mL) and extracted with i-PrOAc (2×25 mL). The combined organic layers were dried over sodium sulfate. The solvent was removed under reduced pressure to obtain the title compound (6 mg, 10%) as colorless liquid, which was sufficiently pure to be used in the next reaction step, MS (EI): m/e=323.3 [M+H]+.

Workup

  1. extractionextracted with i-PrOAc (2×25 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cf6dec799acf41a5bf39a54462f2bf7c
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Linked notes

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