Hydrochloric Acid → 1049660-75-4

HRID 843216Notes

Reaction equation

HRID 843216 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:26]=[CH:25][C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].Cl>CN(C)C=O.O.C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]=[N:10][C:11]2[CH:26]=[CH:25][C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22616839HCID 22616839, compound

Product 1

HCID 226168381049660-75-4Yield 79.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

6.47 g (0.018 mol) of ethyl 5-[4-(4-cyanophenylazo)phenoxy]-pentanoate was dissolved in a mixture of 130 mL of dimethylformamide and 41 mL of water in a 500 mL one-neck round flask fitted with a magnetic stirring bar and a reflux condenser by heating to 90° C. while stirring on an oil bath. 3.9 g (0.098 mol) of NaOH was added through the condenser. Stirring and heating were continued for 1 h after which the reaction mixture was left for cooling to room temperature. The reaction mixture was then diluted with 200 mL of water and acidified with 5.5 N HCl until pH 1.5. The precipitated crude orange product was isolated by filtration. The precipitate was dissolved in 90 mL of hot ethanol and left overnight. After filtration and vacuum drying for 22 h at 50° C. 4.61 g (yield 7.9%) of 5-[4-(4-cyanophenylazo)phenoxy]-pentanoic acid was obtained.

Workup

  1. customfitted with a magnetic stirring bar and a reflux condenser
  2. stirringStirring
  3. temperatureheating
  4. waitafter which the reaction mixture was left
  5. temperaturefor cooling to room temperature
  6. customThe precipitated crude orange product
  7. customwas isolated by filtration
  8. waitleft overnight
  9. filtrationAfter filtration and vacuum
  10. customdrying for 22 h at 50° C

Sources & evidence

ORD record
ord-1bcc323036984965b90def9a5099a63e
Source dataset
uspto-grants-2002_04
Patent number
US06376655B1

Reaction notes

Loading…