Water → HCID 13577664, compound

HRID 1589212Notes

Reaction equation

HRID 1589212 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:13]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:23][C:24](OCC)=[O:25].O.[OH-].[Na+]>O1CCCC1>[NH2:7][C:8]1[C:13]([CH:14]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)[OH:22])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:23][CH2:24][OH:25]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13577658HCID 13577658, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13577664HCID 13577664, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred slurry of 3.3 g (0.087 mole) of lithium aluminum hydride in 75 ml of dry tetrahydrofuran a solution of 15.8 g (0.043 mole) of 2-amino-3-(4-bromobenzoyl) benzeneacetic acid, ethyl ester in 175 ml of tetrahydrofuran was added dropwise over a 20 min period. The mixture was then heated at reflux for 1.5 hr under nitrogen atomsphere. The mixture was cooled and treated successively with 3.3 ml of water, 3.3 ml of a 5% sodium hydroxide solution and 10 ml of water. The mixture was filtered through celite and the filter cake was washed thoroughly with tetrahydrofuran. The combined filtrate and tetrahydrofuran wash was concentrated under reduced pressure to give a solid residue. The solid was recrystallized from ethyl acetate to yield 7.6 g (54%) of the titled compound as gray solid, m.p. 128°-129° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 1.5 hr under nitrogen atomsphere
  3. temperatureThe mixture was cooled
  4. filtrationThe mixture was filtered through celite
  5. washthe filter cake was washed thoroughly with tetrahydrofuran
  6. washThe combined filtrate and tetrahydrofuran wash
  7. concentrationwas concentrated under reduced pressure
  8. customto give a solid residue
  9. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fd24ca794d4748da8ec020b17da2133f
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

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