Methanol → 146422-38-0

HRID 1653719Notes

Reaction equation

HRID 1653719 reaction equation
Cl.[NH2:2][C:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=[O:10])[CH2:5][N:4]=1.S(Cl)([Cl:14])=O.[CH3:16]O>>[ClH:14].[NH2:2][C:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH3:16])=[O:10])[CH2:5][N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 70342994HCID 70342994, compound

Product 1

HCID 45259453146422-38-0Yield 54%

Procedure

2-Amino-3,4,5,6-tetrahydropyridine-5-carboxylic acid HCl (1 g, 5.6 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 589 mg (54%) mp 177°-179° 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 43.63, H 6.75, N 14.56.

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-7086fe14d80f46bcad8343c36dfa4a45
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Reaction notes

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