Water → HCID 13577662, compound

HRID 1589211Notes

Reaction equation

HRID 1589211 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]([Cl: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]([Cl: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 12901252HCID 12901252, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13577662HCID 13577662, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 5.5 g (0.145 mole) of lithium aluminum hydride in 50 ml of dry tetrahydrofuran was added dropwise a solution of 21.9 g (0.069 mole) of 2-amino-3-(4-chlorobenzoyl)benzeneacetic acid, ethyl ester in 120 ml of dry tetrahydrofuran. After the addition was complete, the mixture was heated at reflux under a nitrogen atmosphere for 2.5 hours. The mixture was cooled and treated successively with 5.5 ml of water, 5.5 ml of 5% sodium hydroxide and 16.5 ml of water. The mixture was filtered through celite and the filter cake was washed several times with tetrahydrofuran. The combined filtrates were concentrated to give a solid residue. This residue was recrystallized from ethyl acetate to yield 8.6 g (45%) of the titled compound as fluffy white needles, m.p. 132°-134° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux under a nitrogen atmosphere for 2.5 hours
  4. temperatureThe mixture was cooled
  5. filtrationThe mixture was filtered through celite
  6. washthe filter cake was washed several times with tetrahydrofuran
  7. concentrationThe combined filtrates were concentrated
  8. customto give a solid residue
  9. customThis residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-eac294f0e4ae482bbd1b4746e30da731
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

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