Hydrochloric Acid → (S)-Indoline-2-carboxylic acid ethyl ester

HRID 1590Notes

Reaction equation

HRID 1590 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[C:11]([OH:13])=[O:12].[CH2:14](O)[CH3:15]>>[CH2:14]([O:12][C:11]([C@@H:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:2]1)=[O:13])[CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2733920Indoline-2-carboxylic acid, (S)-

Product 1

HCID 11030625(S)-Indoline-2-carboxylic acid ethyl ester

Procedure

HCl gas was bubbled through a stirring suspension of (S)-indoline-2-carboxylic acid (20 g, 110 mmol) in ethanol (500 mL). When the acid was completely dissolved, the solution was brought to reflux. After 16 hours, the solution was cooled and the solvent removed in vacuo. The residue was triturated with diethyl ether and the resulting off-white solid was collected by filtration, washed with hexanes and dried overnight in a vacuum oven at 30° C. to give (S)-indoline-2-carboxylic acid ethyl ester.HCl (25.7 g, 78%).

Workup

  1. dissolutionWhen the acid was completely dissolved
  2. temperatureto reflux
  3. temperaturethe solution was cooled
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with diethyl ether
  6. filtrationthe resulting off-white solid was collected by filtration
  7. washwashed with hexanes
  8. customdried overnight in a vacuum oven at 30° C.

Sources & evidence

ORD record
ord-d52eb0d907f4438189c898a207603691
Source dataset
uspto-grants-1998_03
Patent number
US05726159

Reaction notes

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