Water → HCID 59255222, compound

HRID 1694094Notes

Reaction equation

HRID 1694094 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[N:12][CH:11]=1.O.[OH-].[Na+]>O1CCCC1>[O:16]([C:14]1[CH:15]=[C:10]([CH2:9][OH:8])[CH:11]=[N:12][CH:13]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 592551745-Phenoxynicotinic acid methyl ester

Product 1

HCID 59255222HCID 59255222, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (689 mg, 14.5 mmol, purity: 80%) in tetrahydrofuran (20 mL) was added 5-phenoxy-nicotinic acid methyl ester (1.11 g, 4.84 mmol) described in Manufacturing Example 145-1-1 at 0° C., which was stirred for 20 minutes at room temperature. First water (689 μL), then a 5 N sodium hydroxide aqueous solution (689 μL), and then water (2.07 mL) were added at 0° C. to the reaction mixture, which was filtered through a Celite pad. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (756 mg, 78%).

Workup

  1. customdescribed in Manufacturing Example 145-1-1 at 0° C.
  2. filtrationwas filtered through a Celite pad
  3. concentrationThe filtrate was concentrated under a reduced pressure
  4. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-93b5ce41ca114589b1df5ab89be364fb
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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