Sodium Hydroxide → HCID 67974141, compound

HRID 1777518Notes

Reaction equation

HRID 1777518 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([O:15]CC)=[O:14])[CH:6]=[CH:7][CH:8]=1)#[N:2].[OH-].[Na+]>O1CCOCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67974167HCID 67974167, compound

Product 1

HCID 67974141HCID 67974141, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 3-(3-cyanophenylamino)benzoate (0.050 g; 0.187 mmol) in dioxane (1 ml) was added a solution of sodium hydroxide (0.022 g; 0.563 mmol) in water (0.6 ml). The mixture was stirred at room temperature for 18 hours and concentrated under reduced pressure to remove the dioxane. The aqueous solution was acidified with 6N hydrochloric acid, extracted with ethyl acetate (2×100 mL), dried and concentrated under reduced pressure to give quantitatively 3-(3-cyanophenylamino)benzoic acid which was directly used in the next step.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the dioxane
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-edf765275fb14f3c8bd638235c995f0c
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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