Methanol → HCID 45264845, compound

HRID 1653722Notes

Reaction equation

HRID 1653722 reaction equation
Cl.[NH2:2][C:3]1[CH2:8][CH:7]([C:9]([OH:11])=[O:10])[CH2:6][CH2:5][N:4]=1.S(Cl)([Cl:14])=O.[CH3:16]O>>[ClH:14].[NH2:2][C:3]1[CH2:8][CH:7]([C:9]([O:11][CH3:16])=[O:10])[CH2:6][CH2:5][N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 70148563HCID 70148563, compound

Product 1

HCID 45264845HCID 45264845, compoundYield 27%

Procedure

2-Amino-3,4,5,6-tetrahydropyridine-4-carboxylic acid HCl (1.54 g, 8.6 mmol) was suspended in anhydrous methanol (100 ml), and thionyl chloride (0.6 ml, 8.6 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 452 mg (27%) mp 180°-181° C., identified as product by 300 MHz nmr and ir 1733 cm-1. Calculated: C 43.64, H 6.8, N 14.55; found: C 43.42, H 6.65, N 14.66.

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-9efa2bef752343cba7fd46a3581add79
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Reaction notes

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