Phenylacetic Acid → HCID 178520234, compound

HRID 48272Notes

Reaction equation

HRID 48272 reaction equation
S(Cl)(Cl)=O.[C:5]1([CH2:11][C:12]([OH:14])=O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1(CC(Cl)=O)C=CC=CC=1.[NH2:25][C:26]1[CH:27]=[N:28][C:29]2[C:34]([C:35]=1[OH:36])=[CH:33][CH:32]=[CH:31][CH:30]=2>ClCCl.O.C(N(CC)CC)C>[OH:36][C:35]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][C:26]=1[NH:25][C:12](=[O:14])[CH2:11][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 999Phenylacetic AcidHCID 7679Phenylacetyl chloride2×HCID 24386Thionyl ChlorideHCID 178507989HCID 178507989, compound

Product 1

HCID 178520234HCID 178520234, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Thionyl chloride (1.5 g) was added dropwise to a cooled solution of phenyl acetic acid (2 g) in dichloromethane (10 mL). This mixture was allowed to stir at ambient temperature for 1 hour to provide a solution containing phenylacetyl chloride. Triethyl amine (4.3 mL) was added to a suspension of 3-aminoquinolin-4-ol in dichloromethane (10 mL) and the resulting mixture was cooled in an ice bath. The phenylacetyl chloride solution was added dropwise to the cooled mixture. The reaction mixture was allowed to stir at ambient temperature overnight. The resulting thick oily precipitate was diluted with water (10 mL) and then stirred rapidly for 1 hour. The reaction mixture was filtered. Thin layer chromatography showed that both the isolated solid and the filtrate contained the desired product. The filtrate was diluted with dichloromethane and water. The dichloromethane layer was separated, dried over magnesium sulfate and then concentrated under vacuum. The residue was combined with the previously isolated solid and recrystallized from 80:20 isopropanol:water to provide 1.3 g of N-(4-hydroxyquinolin-3-yl)phenylacetamide as needles, m.p. 253-255° C. Analysis: Calculated for: C17H14N2O2: %C, 73.37; %H, 5.07; %N, 10.07; Found: %C, 73.16; %H, 5.03; %N, 10.07.

Workup

  1. customto provide a solution
  2. temperaturethe resulting mixture was cooled in an ice bath
  3. stirringto stir at ambient temperature overnight
  4. stirringstirred rapidly for 1 hour
  5. filtrationThe reaction mixture was filtered
  6. additionThe filtrate was diluted with dichloromethane and water
  7. customThe dichloromethane layer was separated
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under vacuum
  10. customrecrystallized from 80:20 isopropanol

Sources & evidence

ORD record
ord-fb65481bace64763b4748bbbc32d72d3
Source dataset
uspto-grants-2004_03
Patent number
US06703402B2

Reaction notes

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