Hydrochloric Acid → 2-(4-(Pyridazin-4-yl)phenyl)acetic acid

HRID 592134Notes

Reaction equation

HRID 592134 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16]CC)=[O:15])=[CH:9][CH:8]=2)=[CH:3][N:2]=1.[OH-].[Na+].O.Cl>O1CCOCC1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:11][CH:12]=2)=[CH:3][N:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58447860HCID 58447860, compound

Product 1

HCID 584479312-(4-(Pyridazin-4-yl)phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(4-(pyridazin-4-yl)phenyl)acetate 37-3 (150 mg, 0.62 mmol) and NaOH (120 mg, 3 mmol) was mixed in dioxane (1.5 mL) and H2O (1.5 mL) and stirred at 80° C. for 1 hour. After cooled down to 0° C., the mixture was treated with 1 N HCl aqueous solution to pH 1, and taken to dryness by rotary evaporation. The crude product was extracted with ethyl acetate (100 mL×3). The combined organic phases were concentrated to give 2-(4-(pyridazin-4-yl)phenyl)acetic acid 37-4 as pale yellow solid. MS m/z 215.1 (M+1)

Workup

  1. customtaken to dryness by rotary evaporation
  2. extractionThe crude product was extracted with ethyl acetate (100 mL×3)
  3. concentrationThe combined organic phases were concentrated

Sources & evidence

ORD record
ord-8cb385b4e9ea460a8f66ff08ce5b8e97
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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