HCID 23320874, compound → HCID 19764523, compound

HRID 280551Notes

Reaction equation

HRID 280551 reaction equation
[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][N:5]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:6]1[N:11]=[C:10](/[CH:12]=[CH:13]/[C:14]([O:16]CC)=[O:15])[CH:9]=[CH:8][CH:7]=1>CO.[OH-].[K+]>[CH3:28][N:2]([CH3:1])[CH2:3][CH2:4][N:5]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[C:6]1[N:11]=[C:10](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 23320874HCID 23320874, compound

Product 1

HCID 19764523HCID 19764523, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

The ester from above (297 mg, 0.77 mmol) was dissolved in 10 mL of methanol with 4 mL of 1M potassium hydroxide and stirred overnight at room temperature. The solvent was removed under vacuum and the residue was redissolved in 20 mL of water and extracted with two 20 mL portions of ether. The aqueous layer was adjusted to a pH of 7 with 1M hydrochloric acid and the powdery precipitate was collected by filtration to give 165 mg of (E)-3-(6-(N-(2-dimethylaminoethyl)-4-methoxybenzylamino)-2-pyridyl)acrylic acid as the dihydrate, mp. 75°-81°. Calc. for C20H25N3O3.2H2O: C, 61.36; H, 7.47; N, 10.73. Found: C, 61.26; H, 7.44; N, 10.67.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was redissolved in 20 mL of water
  3. extractionextracted with two 20 mL portions of ether
  4. filtrationthe powdery precipitate was collected by filtration

Sources & evidence

ORD record
ord-1ff62fdd192d4e9aa0f309eabeaab784
Source dataset
uspto-grants-1986_05
Patent number
US04590199

Reaction notes

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