Methanol → HCID 45261143, compound

HRID 1681889Notes

Reaction equation

HRID 1681889 reaction equation
Cl.[NH2:2][C:3]1[CH:8]([C:9]([OH:11])=[O:10])[CH2:7][CH2:6][CH2:5][N:4]=1.S(Cl)([Cl:14])=O.[CH3:16]O>>[ClH:14].[NH2:2][C:3]1[CH:8]([C:9]([O:11][CH3:16])=[O:10])[CH2:7][CH2:6][CH2:5][N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 70342450146422-39-1

Product 1

HCID 45261143HCID 45261143, compoundYield 46%

Procedure

2-Amino-3,4,5,6-tetrahydropyridine-3-carboxylic acid HCl (1.2 g, 6.6 mmol) was suspended in anhydrous methanol (100 ml), and thionyl chloride (0.5 ml, 7 mmol) was added dropwise with stirring at room temperature. The resulting solution was refluxed overnight and then evaporated to dryness in vacuo. The resulting crude white solid was recrystallized from methanol/ether to give white crystals 613 mg (46%) mp 138°-139° C., identified as product by 300 MHz nmr and ir 1737 cm-1. Calculated: C 43.64, H 6.8, N 14.55; found: C 43.75, H 6.87, N 14.57.

Workup

  1. temperatureThe resulting solution was refluxed overnight
  2. customevaporated to dryness in vacuo
  3. customThe resulting crude white solid was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-e61adcb4c3914552aa4248ee0abea183
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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