4-Amino-2-chlorobenzonitrile → HCID 86729771, compound

HRID 2272613Notes

Reaction equation

HRID 2272613 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[CH:11]12[CH2:17][CH2:16][CH:15]1[C:14](=[O:18])[O:13][C:12]2=[O:19]>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[Cl:10][C:4]1[CH:3]=[C:2]([NH:1][C:14]([CH:15]2[CH2:16][CH2:17][CH:11]2[C:12]([OH:19])=[O:13])=[O:18])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 887284-Amino-2-chlorobenzonitrileHCID 1382613-Oxabicyclo(3.2.0)heptane-2,4-dione

Product 1

HCID 86729771HCID 86729771, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4-amino-2-chlorobenzonitrile (1229 mg, 8.06 mmol), 3-oxabicyclo[3.2.0]heptane-2,4-dione (1016 mg, 8.06 mmol) and TEA (1.123 mL, 8.06 mmol) in toluene (10 mL) was stirred at 80° C. for 14 hr. To the reaction mixture was added brine at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by COOH-silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane), and crystallized from ethyl acetate to give 2-((3-chloro-4-cyanophenyl)carbamoyl)cyclobutanecarboxylic acid (795 mg, 2.85 mmol, 35.4%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by COOH-silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)
  6. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-28264ea4823641ddba49e35a9ed78951
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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