Sodium Hydroxide → HCID 86752022, compound

HRID 861324Notes

Reaction equation

HRID 861324 reaction equation
C([O:3][C:4](=[O:25])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:9][CH:8]=1)=[CH2:6])C.[OH-].[Na+]>C(O)C>[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:5](=[CH2:6])[C:4]([OH:25])=[O:3])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86752021HCID 86752021, compound

Product 1

HCID 86752022HCID 86752022, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution in hot ethanol of 3,3-bis((4-(2-quinolylmethoxy)phenyl)-propenoic acid ethyl ester (560 mg, 1 mmol), prepared as in step 1, was added aqueous 1N NaOH (8 mL) and the reaction mixture was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature, concentrated in vacuo, diluted with water (25 mL), and neutralized with 10% citric acid solution. The resulting precipitate was collected by filtration, washed with water, slurried in warm EtOH (20 mL), collected by filtration, and dried in vacuo to obtain 3,3-bis((4-(2-quinolyl-methoxy)phenyl)propenoic acid (265 mg): mp 127°-130° C.; 1H NMR (300 MHz, DMSO-d6)δ5.40 (s, 4H), 6.20 (s, 1H), 7.08 (m, 6H), 7.21 (d, 2H, J=9 Hz), 7.73 (m, 6H), 8.03 (m, 4H), 8.44 (t, 2H, J=9 Hz), 11.97 (bs, 1H); MS (DCI/NH3) m/e 538 (M+H)+. Anal. Calcd. for C35H26 N3O5 ×3H2O: C, 70.95; H, 5.41; N, 4.73. Found: C, 70.53; H, 5.24; N, 4.61.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. additiondiluted with water (25 mL)
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. filtrationcollected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d8642b2e944e48f4a44eab7f63e239e7
Source dataset
uspto-grants-1998_02
Patent number
US05714488

Reaction notes

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