Methanol → Methyl indoline-2-carboxylate

HRID 1642127Notes

Reaction equation

HRID 1642127 reaction equation
S(Cl)(Cl)=O.[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[C:14]([OH:16])=[O:15].[CH3:17]O>>[CH3:17][O:15][C:14]([CH:6]1[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:5]1)=[O:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 86074Indoline-2-carboxylic acid

Product 1

HCID 2794655Methyl indoline-2-carboxylate

Procedure

Thionyl chloride (12.1 ml, 167.2 mmol) was added dropwise, with stirring and while cooling with ice, to a solution of indoline-2-carboxylic acid (24.8 g, 152.0 mmol) in methanol (500 ml). The reaction mixture was stirred overnight at 40° C. The reaction solution was concentrated and thionyl chloride residues were removed by dragging out with diethyl ether (3 times).

Workup

  1. stirringThe reaction mixture was stirred overnight at 40° C
  2. concentrationThe reaction solution was concentrated
  3. customthionyl chloride residues were removed

Sources & evidence

ORD record
ord-902c4f690c734653a04703623f30024d
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

Loading…