Hydrochloric Acid → Ethyl indoline-2-carboxylate

HRID 1720001Notes

Reaction equation

HRID 1720001 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[C:10]([OH:12])=[O:11].[ClH:13].[CH2:14](O)[CH3:15]>>[ClH:13].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[C:10]([O:12][CH2:14][CH3:15])=[O:11]

Participants

4

Reactant 3

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

Product 1

HCID 22822759Ethyl indoline-2-carboxylate

Procedure

A suspension of (S)-indoline-2-carboxylic acid (6.02 g., 36.9 mmol.) in ethanol (70 ml.) at 0° was saturated with hydrochloric acid and allowed to warm to room temperature. After 3 hours at room temperature, the resulting clear, red solution was purged with nitrogen and diluted with ethyl ether (200 ml.). The crystallized product was collected, washed with ethyl ether and dried in vacuo to give 6.43 g. of the title compound as white needles, m.p. 168°-169°; α!D =-70.7° (c=0.68, chloroform). TLC (ethyl acetate-hexane, 1:1) Rf =0.63 (as free base).

Workup

  1. customthe resulting clear, red solution was purged with nitrogen
  2. additiondiluted with ethyl ether (200 ml.)
  3. customThe crystallized product was collected
  4. washwashed with ethyl ether
  5. customdried in vacuo
  6. customto give 6.43 g

Sources & evidence

ORD record
ord-2341f1275cda4573a992c40ec7d37def
Source dataset
uspto-grants-1996_04
Patent number
US05504080

Reaction notes

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