Hydrochloric Acid → HCID 21291582, compound

HRID 590398Notes

Reaction equation

HRID 590398 reaction equation
N[C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.Cl.N([O-])=O.[Na+].[Cu](C#N)[C:20]#[N:21].[C-]#N.[Na+]>O.C(OCC)(=O)C>[Cl:11][C:10]1[C:2]([C:20]#[N:21])=[CH:3][C:4]([O:12][CH3:13])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 23668193Sodium NitriteHCID 178418260HCID 178418260, compound

Product 1

HCID 21291582HCID 21291582, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 4-amino-5-chloro-2-methoxybenzoic acid (4 g, 0.019 mol) in water (60 mL) was added hydrochloric acid (35%, 0.63 mL) and the mixture was stirred vigorously and cooled to 5° C. Then a solution of sodium nitrite (1.92 g, 0.027 mol) in water (6 mL) was added dropwise. The mixture was stirred for some minutes and then a previously formed solution of copper cyanide (2.32 g, 0.026 mol) and sodium cyanide (3.65 g, 0.074 mol) in water (20 mL) was added dropwise maintaining a low temperature. Once the addition was finished the reaction mixture was stirred 1 hour at room temperature. The pH of the aqueous phase was adjusted to 3 and ethyl acetate was added into the mixture and the organic layer was washed with water, dried, filtered and the solvent was removed under reduced pressure giving the title compound (2.93 g, 62%).

Workup

  1. stirringThe mixture was stirred for some minutes
  2. temperaturemaintaining a low temperature
  3. additionOnce the addition
  4. stirringwas stirred 1 hour at room temperature
  5. additionwas added into the mixture
  6. washthe organic layer was washed with water
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-727a675baed145f4a30fdba9925c10cc
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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