HCID 18537637, compound → HCID 18537635, compound

HRID 412383Notes

Reaction equation

HRID 412383 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13](OC)=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.[OH-].[Na+]>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:12][CH2:13][OH:14])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:9])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 18537637HCID 18537637, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 18537635HCID 18537635, compoundYield 105.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 2-(3-amino-4-t-butylphenyl)acetate (11.1 g) in anhydrous tetrahydrofuran (70 ml) was added dropwise to a suspension of lithium aluminium hydride (4.0 g) in anhydrous tetrahydrofuran (150 ml) over a period of 15 minutes. The mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with tetrahydrofuran (150 ml) and aqueous sodium hydroxide solution (15%) was added to the mixture while cooling in an ice bath in order to decompose the excess lithium aluminium hydride. The insoluble material was filtered off through Celite (trademark) and the solvent of the filtrate was evaporated under reduced pressure to afford the desired compound 10.2 g, Rf=0.49: thin layer chromatography on a silica gel plate using n-hexane:ethyl acetate=1:3 as the eluant).

Workup

  1. additionwas added to the mixture
  2. temperaturewhile cooling in an ice bath in order
  3. filtrationThe insoluble material was filtered off through Celite (trademark)
  4. customthe solvent of the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e346ddb9299d4e41bef0e37a5f11f404
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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