Sodium Hydroxide → HCID 14279613, compound

HRID 2231318Notes

Reaction equation

HRID 2231318 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][CH2:6][C:7](=[O:24])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:9]=1[NH2:23])C.[OH-].[Na+]>C(O)C>[NH2:23][C:9]1[C:10]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:11][CH:12]=[CH:13][C:8]=1[C:7](=[O:24])[CH2:6][CH2:5][C:4]([OH:25])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14279612HCID 14279612, compound

Product 1

HCID 14279613HCID 14279613, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.3 g (0.0092 mole) of 2-amino-3-(4-chlorobenzoyl)-γ-oxobenzenebutanoic acid ethyl ester in 70 ml of hot 190 proof ethanol was treated with 40 ml of 4N aqueous sodium hydroxide solution and the mixture was heated at reflux for 18 hr. The hot mixture was filtered and the insoluble material was discarded. The filtrate was cooled and the precipitate collected by filtration. This precipitate was partitioned between dilute hydrochloric acid and methylene chloride. The organic layer was separated, dried over magnesium sulfate and concentrated to give 2.7 g (89%) of bright yellow crystals, m.p. 172°-177° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hr
  3. filtrationThe hot mixture was filtered
  4. temperatureThe filtrate was cooled
  5. filtrationthe precipitate collected by filtration
  6. customThis precipitate was partitioned between dilute hydrochloric acid and methylene chloride
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-189c2a99ae0c425d8d5123ea59a610b9
Source dataset
uspto-grants-1988_11
Patent number
US04782089

Reaction notes

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