Hydrochloric Acid → Indoline-2-carboxylic acid, (S)-

HRID 4736Notes

Reaction equation

HRID 4736 reaction equation
CC1CCCC(C)N1.Cl[CH:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[C:11]([OH:13])=[O:12].[OH-].[Na+].Cl>CN(C=O)C>[NH:21]1[C:16]2[C:15](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13651766(+)-alpha-Chloro-2-aminobenzenepropanoic acid 2,6-dimethylpiperidine salt

Product 1

HCID 2733920Indoline-2-carboxylic acid, (S)-Yield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(+)-α-Chloro-2-aminobenzenepropanoic acid 2,6-dimethylpiperidine salt (1.25 g., 4.00 mmol) was added to magnetically stirred N sodium hydroxide (4 ml.) under nitrogen. The solution was stirred under nitrogen overnight at room temperature. The pH was adjusted to a value between 2 and 3 (pH paper) with conc. hydrochloric acid while cooling in ice. The crystalline precipitate was collected and washed with several aliquots of ice cold water. The product was dried briefly under vacuum over phosphorus pentoxide and then stirred with ether. The product was dried over phosphorus pentoxide at 56° C. for several hours under oil pump vacuum to give 0.48 g. (74%) of the title compound, m.p. 155°-157° C., [α]D25 +36.09° (c 0.87, DMF).

Workup

  1. temperaturewhile cooling in ice
  2. customThe crystalline precipitate was collected
  3. washwashed with several aliquots of ice cold water
  4. dry with materialThe product was dried briefly under vacuum over phosphorus pentoxide
  5. stirringstirred with ether
  6. dry with materialThe product was dried over phosphorus pentoxide at 56° C. for several hours under oil pump vacuum
  7. customto give 0.48 g

Sources & evidence

ORD record
ord-bbaa8fd2fc2a4f12ab8b5fe533c40c1c
Source dataset
uspto-grants-1988_02
Patent number
US04727183

Reaction notes

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