Triethylamine → Coumarin, 3-(2-benzoylethyl)-4-hydroxy-

HRID 1721385

Reaction equation

HRID 1721385 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.CN(C)[CH:15]([CH3:24])[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].C(N(CC)CC)C.[OH-].[Na+]>C(#N)C>[OH:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:5][C:4](=[O:12])[C:3]=1[CH2:24][CH2:15][C:16](=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 71872MetamfepramoneHCID 546829304-Hydroxycoumarin

Product 1

HCID 54686119Coumarin, 3-(2-benzoylethyl)-4-hydroxy-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.81 g (5.0 mmol) of 4-hydroxycoumarin, 1.07 g (5.0 mmol) of 2-dimethylaminopropiophenone, and 20 mL of acetonitrile was treated with 0.2 mL (5.0 mmol) of triethylamine and then refluxed for 4 hours. The mixture was cooled to room temperature and poured into 5% sodium hydroxide. The aqueous solution was extracted with ether and acidified to pH 3 with 6N hydrochloric acid. The mixture was extracted with chloroform, and the extract was washed with water, dried, and concentrated to give the title compound, m.p. 149°-151° C. NMR (CDCl3) δ2.99 (m, 2H), 3.52 (m, 2H), 7.26 (m, 2H), 7.48 (m, 3H), 7.60 (m, 1H), 7.94 (dd, 1H), 8.02 (d, 2H), 10.65 (bs, 1H).

Workup

  1. temperaturerefluxed for 4 hours
  2. extractionThe aqueous solution was extracted with ether
  3. extractionThe mixture was extracted with chloroform
  4. washthe extract was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f5b874ee69ea495dba5014bfe97c8f88
Source dataset
uspto-grants-1996_04
Patent number
US05510375

Linked notes

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