Methanol → Methyl indoline-2-carboxylate

HRID 1601074Notes

Reaction equation

HRID 1601074 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>>[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 3

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

Product 1

HCID 2794655Methyl indoline-2-carboxylateYield 94%

Procedure

Thionyl chloride (2.86 mL, 39 mmol) was added to a solution of (±)-indoline-2-carboxylic acid (4.26 g, 26 mmol) in methanol (30 mL) at 0° C. The resulting mixture was stirred at RT for 18 h. The solvent was removed in vacuo and the residue was taken into CH2Cl2 and washed sequentially with H2O and saturated NaCl. Drying (MgSO4) and concentration gave the title compound (4.31 g, 94%) as a pale yellow oil.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed sequentially with H2O and saturated NaCl
  3. customDrying
  4. concentration(MgSO4) and concentration

Sources & evidence

ORD record
ord-e228957e4ea04888b5c576e7a20e3036
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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