Hydrochloric Acid → Ethyl 2-(3-aminophenyl)acetate

HRID 890600Notes

Reaction equation

HRID 890600 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.ClCCl.Cl.[CH2:20](O)[CH3:21]>C(OCC)C>[CH2:20]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=1)[CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 571807(3-Aminophenyl)acetic acid

Product 1

HCID 13042040Ethyl 2-(3-aminophenyl)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a cooled solution (−15° C.) of 3-aminophenylacetic acid (10.2, 67 mmol) in ethanol (200 mL) was added dropwise thionyl chloride (10 mL, 0.14 mol). The reaction mixture was stirred for 24 h allowing the temperature to slowly rise to rt. Evaporation of the volatiles gave a beige solid that was stripped several times with dichloromethane. The solid was then treated with hot diethyl ether and filtered to remove diethyl sulphite. Recrystallization from dietyl ether gave 14.4 g, 67 mmol, 100% of the desired compound as an off-white crystalline hydrochloride, mp 135° C. IR (KBr) cm−1 2857,2614, 1740

Workup

  1. customto slowly rise to rt
  2. customEvaporation of the volatiles
  3. customgave a beige solid
  4. filtrationfiltered
  5. customto remove diethyl sulphite
  6. customRecrystallization from dietyl ether

Sources & evidence

ORD record
ord-d8ca5abc20014ced8e49b421cd4ab4d8
Source dataset
uspto-grants-2006_02
Patent number
US06998405B2

Reaction notes

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