4-Cyanobenzoic acid → HCID 60637584, compound

HRID 2272588Notes

Reaction equation

HRID 2272588 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:9])=[CH:10][CH:11]=1)#[N:2]

Participants

7

Reactant 4

HCID 120874-Cyanobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 126496614-Aminobutyrate ethyl hydrochloride

Product 1

HCID 60637584HCID 60637584, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-cyanobenzoic acid (2.0 g, 13.59 mmol), ethyl 4-aminobutyrate hydrochloride (2.507 g, 14.95 mmol), HOBt (0.918 g, 6.80 mmol) and TEA (6.63 mL, 47.58 mmol) in DMF (20 mL) was added WSC (3.26 g, 16.99 mmol), and the mixture was stirred at room temperature for 14 hr. Water was poured into the reaction mixture, 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 silica gel column chromatography (solvent gradient; 5 to 75% ethyl acetate/hexane) to give ethyl 4-(4-cyanobenzamido)butanoate (1.558 g, 5.99 mmol, 44.0%) as a white powder.

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 silica gel column chromatography (solvent gradient; 5 to 75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-95d42799a75049a590f3ff3ad0a9400e
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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