Hydrochloric Acid → HCID 58538388, compound

HRID 539865Notes

Reaction equation

HRID 539865 reaction equation
[OH-:1].[Na+].BrBr.[C:5]([C:8]1[CH:9]=[CH:10][C:11]([O:16][CH2:17][CH2:18][CH3:19])=[C:12]([CH:15]=1)[C:13]#[N:14])(=[O:7])C.Cl>O.O1CCOCC1>[C:13]([C:12]1[CH:15]=[C:8]([CH:9]=[CH:10][C:11]=1[O:16][CH2:17][CH2:18][CH3:19])[C:5]([OH:7])=[O:1])#[N:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 86659944HCID 86659944, compound

Product 1

HCID 58538388HCID 58538388, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

NaOH (5.52 g, 0.138 mol) was dissolved in water (35 ml) under ice-bath, followed by slow addition of liquid bromine (3.5 ml, 0.068 mol) under cooling. After a solution of 5-acetyl-2-n-propoxybenzonitrile (7 g, 0.034 mol) in dioxane (35 ml) was slowly added dropwise thereto, the reaction continued for 2 h. The reaction mixture was adjusted slowly to a pH of about 2 with a diluted hydrochloric acid to generate a large amount of light yellow solid. After filtered, the resultant solid was washed with ethyl acetate, and filtered to obtain the title compound (6.5 g, yield: 92%). 1H NMR (CDCl3) δ: 13.21 (1H, br), 8.18 (1H, d), 8.15 (1H, dd), 7.34 (1H, d), 4.18 (2H, t), 1.79 (2H, m), 1.00 (3H, t).

Workup

  1. temperatureunder cooling
  2. filtrationAfter filtered
  3. washthe resultant solid was washed with ethyl acetate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9eea6a5ce7154077abf3ab35f0664921
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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