Hydrochloric Acid → Methyl 4-(2-acetylaminophenyl)butanoate

HRID 1242902

Reaction equation

HRID 1242902 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24].Cl>O1CCCC1.C(OCC)(=O)C>[C:23]([NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:25])[CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21940035Methyl 4-(2-aminophenyl)butanoate hydrochloride

Product 1

HCID 21939908Methyl 4-(2-acetylaminophenyl)butanoateYield 73.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-(2-aminophenyl)butanoate hydrochloride (7.20 g, 0.037 mol) synthesized by a known method by documents (Synthetic communications, 26(18), 3443 (1996)) and triethylamine (5.06 g, 0.05 mol) were dissolved in tetrahydrofuran (60 ml). Acetyl chloride (3.51 g, 0.045 mol) was added dropwise to the mixture, which was stirred at room temperature for 30 minutes. Ethyl acetate and 1N hydrochloric acid were added to the reaction mixture, and extraction was conducted. The organic layer was washed with water, concentrated and dried. A mixed solution of ethyl acetate-n-hexane (1:1) was added to the residue. The crystallized product was collected by filtration, to give methyl 4-(2-acetylaminophenyl)butanoate (6.40 g) as a white powder.

Workup

  1. washThe organic layer was washed with water
  2. concentrationconcentrated
  3. customdried
  4. additionA mixed solution of ethyl acetate-n-hexane (1:1) was added to the residue
  5. filtrationThe crystallized product was collected by filtration

Sources & evidence

ORD record
ord-8965cf46fabd464d87d6ed70456b2500
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Linked notes

Loading…