Ethanol → 1h-Indole-3-acetic acid,2-phenyl-,ethyl ester

HRID 1591345Notes

Reaction equation

HRID 1591345 reaction equation
[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.OS(O)(=O)=O.[CH2:27](O)[CH3:28]>>[C:10]1([C:9]2[NH:7][C:1]3[C:6]([C:17]=2[CH2:18][C:19]([O:21][CH2:27][CH3:28])=[O:20])=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7516PhenylhydrazineHCID 728713-Benzoylpropionic acid

Product 1

HCID 125026691h-Indole-3-acetic acid,2-phenyl-,ethyl esterYield 73%

Procedure

Phenylhydrazine (80 mmol), 3-benzoylpropionic acid (1a) (80 mmol), and 12 ml of concentrated H2SO4 in 100 ml of ethanol were heated at reflux for 24 hours. The cooled reaction mixture was poured onto 500 g of ice, and the resulting mixture was extracted with ether (300 ml×2). Workup gave a red oil, which was purified by column chromatography (silica gel, ethyl acetate/n-hexane=1/5) to afford 15.2 g (73%) of ethyl 2-phenyl-3-indole acetate (8) as a pale yellow solid. mp: 61°-62° C.; IR (KBr) 3370, 1718, 1585, 1458 cm-1 ; 1H NMR (CDCl3, 300 MHz), 8 8.17 (s, 1H), 7.67-7.71 (m, 3H), 7.47 (dd, 2H), 7.40 (dd, 2H), 7.40 (dd, 2H), 7.20 (m, 2H), 4.12 (q, 2H), 3.98 (s, 2H), 1.07 (t, 3H), mass spectrum (15 ev) m/Z 279 (M), 206, 179, 128, 102, 77, 58, 43; exact mass calcd for C18H17NO2 279.1259; found 279.1259.

Workup

  1. temperatureat reflux for 24 hours
  2. customThe cooled reaction mixture
  3. extractionthe resulting mixture was extracted with ether (300 ml×2)
  4. customWorkup gave a red oil, which
  5. customwas purified by column chromatography (silica gel, ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-9c4482adbfba4cd389b73a0ad4ff2661
Source dataset
uspto-grants-1993_04
Patent number
US05206382

Reaction notes

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