Hydrochloric Acid → 3-Chloro-n-(4-methoxyphenyl)propanamide

HRID 431810Notes

Reaction equation

HRID 431810 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[OH-].[Na+].[Cl:12][CH2:13][CH2:14][C:15](Cl)=[O:16].Cl>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:15](=[O:16])[CH2:14][CH2:13][Cl:12])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 693643-Chloropropionyl chloride

Product 1

HCID 5320593-Chloro-n-(4-methoxyphenyl)propanamideYield 139.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

p-Anisidine (12.3 g) was dissolved in CH2Cl2 (30 ml) and the solution was cooled to −5° C. Aqueous NaOH (6.6 g in 13 ml water) and 3-chloro-propionyl-chloride (19.05 g) were simultaneous added to the above solution over 40 minutes. The two phase mixture was stirred at 5° C. for another 30 mm. Water (250 ml) and concentrated HCl (3 ml) were then added. The product was isolated by filtration, washed with water and dried to a constant weight to give N-(4-methoxyphenyl)-3-chloropropionamide (29.7 g, 94.6%) in 99.3% purity by HPLC analysis.

Workup

  1. customThe product was isolated by filtration
  2. washwashed with water
  3. customdried to a constant weight

Sources & evidence

ORD record
ord-6bcf9c0860d2445e9fe479993b079a32
Source dataset
uspto-grants-2003_12
Patent number
US06660773B2

Reaction notes

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