Water → HCID 21111446, compound

HRID 425945Notes

Reaction equation

HRID 425945 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH2:27])=[C:14]([O:16][CH2:17][C:18]3[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=3[Cl:26])[CH:15]=2)=[CH:6][CH:5]=1.O.[Li+].[OH-]>C(O)(C)C.CCOC(C)=O.[Cl-].[Na+].O>[NH2:27][C:13]1[N:12]=[CH:11][C:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:28])=[O:2])=[CH:9][CH:8]=2)=[CH:15][C:14]=1[O:16][CH2:17][C:18]1[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=1[Cl:26]

Participants

7

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 66701762HCID 66701762, compound

Product 1

HCID 21111446HCID 21111446, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 4-[6-amino-5-(2-chloro-3,6-difluoro-benzyloxy)-pyridin-3-yl]-benzoic acid methyl ester (2.5 g, 6 mmol) in warm isopropanol (300 mL) was added H2O (100 mL) containing LiOH (0.74 g, 31 mol). The reaction immediately turned orange and was left to stir at room temperature for 18 hr. The reaction was diluted with EtOAc (200 mL) and brine (50 mL). The organic was separated off and the aqueous was extracted with EtOAc (2×50 mL). The organic layers were combined and washed with brine (2×25 mL), dried with Na2SO4 and concentrated to dryness under vacuum to yield 4-[6-amino-5-(2-chloro-3,6-difluoro-benzyloxy)-pyridin-3-yl]-benzoic acid (2.4 g, 6 mmol, 99%) as an off-white solid.

Workup

  1. customThe reaction immediately turned orange
  2. waitwas left
  3. customThe organic was separated off
  4. extractionthe aqueous was extracted with EtOAc (2×50 mL)
  5. washwashed with brine (2×25 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-537abf7b8b3842fd9e3705906a701282
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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