Water → HCID 131722560, compound

HRID 1977166Notes

Reaction equation

HRID 1977166 reaction equation
[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)[CH3:4].[O:16]=[C:17]([OH:29])[C@@H:18]([C@H:20]([C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23])[OH:21])[OH:19].O>C(O)C>[O:16]=[C:17]([OH:29])[C@@H:18]([C@H:20]([C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23])[OH:21])[OH:19].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)[CH3:4].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9855809HCID 9855809, compound

Product 1

HCID 131722560HCID 131722560, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

(4E)-N-Methyl-5-(5-methoxy-3-pyridyl)4-penten-2-amine (1.20 g, 5.83 mmol) was dissolved in ethyl alcohol (20 mL), assisted by warming to 60° C. The warm solution was treated with galactaric acid (610 mg, 2.91 mmol) in one portion, followed by dropwise addition of water (0.5 mL). The solution was filtered while hot to remove some insoluble material. The filtrate was allowed to cool to ambient temperature. The resulting crystals were filtered, washed with anhydrous diethyl ether, and dried under vacuum at 40° C. to yield 1.05 g (58.0%) of a white, crystalline powder, mp 143-145° C.

Workup

  1. filtrationThe solution was filtered while hot
  2. customto remove some insoluble material
  3. temperatureto cool to ambient temperature
  4. filtrationThe resulting crystals were filtered
  5. washwashed with anhydrous diethyl ether
  6. customdried under vacuum at 40° C.
  7. customto yield 1.05 g (58.0%) of a white, crystalline powder, mp 143-145° C.

Sources & evidence

ORD record
ord-839319fbea27426c82a3b4a6f90fef6d
Source dataset
uspto-grants-2001_05
Patent number
US06232316B1

Reaction notes

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