Methanol → HCID 12773702, compound

HRID 1578091Notes

Reaction equation

HRID 1578091 reaction equation
Cl.[CH2:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]([C:15]([OH:17])=[O:16])[CH2:4][NH:3]1.S(Cl)([Cl:20])=O.[CH3:22]O>>[ClH:20].[CH2:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]([C:15]([O:17][CH3:22])=[O:16])[CH2:4][NH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 70455578HCID 70455578, compound

Product 1

HCID 12773702HCID 12773702, compound

Conditions

Temperature
0 °C

Procedure

1,2,3,4-Tetrahydro-β-carboline-4-carboxylic acid hydrochloride (3 g, 0.012 mole) (TR-8025) prepared in Example 3 was mixed with 50 ml of methanol. It was cooled at 0° C. Then thionylchloride (2 ml, 0.028 mole) was added dropwise. The mixture was stirred at room temperature for 24 hours. The solvent was removed in vacuo. The residue was partitioned in ethyl acetate/6% K2CO3 solution. The organic phase was dried over MgSO4, filtered and treated with 4 NHCl in dioxane to pH=5. A white solid was collected. Yield: 2 g (62%) mp 246°-247° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was partitioned in ethyl acetate/6% K2CO3 solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. additiontreated with 4 NHCl in dioxane to pH=5
  6. customA white solid was collected

Sources & evidence

ORD record
ord-a68752e0cd5a4f1a8c2f42182a45c0cd
Source dataset
uspto-grants-1981_09
Patent number
US04291039

Reaction notes

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