Sodium Hydroxide → HCID 10356293, compound

HRID 1609052Notes

Reaction equation

HRID 1609052 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:20])[C:14]([C:16]([O:18]C)=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH3:21].[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:20])[C:14]([C:16]([OH:18])=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19788691HCID 19788691, compound

Product 1

HCID 10356293HCID 10356293, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.3 g (18 mmol) of methyl ester (6) obtained in Example 2 (1) was added to 250 ml of tetrahydrofuran, and, while the solution was heated under reflux, 100 ml of aqueous solution containing 0.76 g (19 mmol) of sodium hydroxide was added to the solution. The obtained solution was heated under reflux for 1.5 hours. After air-cooled, while cooling on ice, the solution was neutralized with 4.2 g (20 mmol) of citric hydrate and stirred for 1 hour. The solid was filtered off and washed consecutively with water, ethanol and ether to obtain 3.78 g of the subject compound (8) in a 75% yield. The result of the analysis of this compound was as follows.

Workup

  1. temperaturewhile the solution was heated
  2. temperatureunder reflux
  3. additionwas added to the solution
  4. temperatureThe obtained solution was heated
  5. temperatureunder reflux for 1.5 hours
  6. temperatureAfter air-cooled
  7. temperaturewhile cooling on ice
  8. filtrationThe solid was filtered off
  9. washwashed consecutively with water, ethanol and ether

Sources & evidence

ORD record
ord-02bdc6dfeea64aa1baab77cc08d634ad
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

Loading…