Methanol → HCID 45261119, compound

HRID 1653724Notes

Reaction equation

HRID 1653724 reaction equation
Cl.[NH2:2][C:3]1[CH2:8][CH2:7][CH2:6][CH:5]([C:9]([OH:11])=[O:10])[N:4]=1.S(Cl)([Cl:14])=O.[CH3:16]O>>[ClH:14].[NH2:2][C:3]1[CH2:8][CH2:7][CH2:6][CH:5]([C:9]([O:11][CH3:16])=[O:10])[N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 70342222HCID 70342222, compound

Product 1

HCID 45261119HCID 45261119, compoundYield 31%

Procedure

2-Amino-3,4,5,6-tetrahydropyridine-6-carboxylic acid HCl (1.99 g, 11.1 mmol) was suspended in anhydrous methanol (100 ml), and thionyl chloride (0.8 ml, 11.1 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 ethanol to give white crystals 656 mg (31%) mp 132°-134° C., identified as product by 300 MHz nmr and ir 1753 cm-1. Calculated: C 43.64, H 6.8, N 14.55; found: C 43.80, H 6.81, N 14.46.

Workup

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

Sources & evidence

ORD record
ord-74e69cc267c1487596351b400cccac57
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Reaction notes

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