Hydrochloric Acid → Isoindoline-4-carboxylic acid

HRID 1826993Notes

Reaction equation

HRID 1826993 reaction equation
Cl.C[O:3][C:4]([C:6]1[C:7]2[CH2:8][NH:9][CH2:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:5].[OH-].[Li+].Cl>CO.C1COCC1.O>[CH2:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:6]([C:4]([OH:5])=[O:3])[C:7]=2[CH2:8][NH:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 19828511Methyl 2,3-dihydro-1H-isoindole-4-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 10329608Isoindoline-4-carboxylic acidYield 4.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a suspension of the 2,3-dihydro-1H-isoindole-4-carboxylic acid methyl ester hydrochloride salt (0.18 g, 0.83 mmol) in 25% MeOH/THF (4 ml) was added dropwise lithium hydroxide (0.08 g, 3.32 mmol) in water (1 ml), followed by addition of water (2 ml) and the clear solution stirred at room temperature under nitrogen for 5 h. The solution was acidified with aq. HCl. and purified by ion-exchange (DOWEX™ 50WX2-100) resin eluting with a solvent gradient of ammonia:water (5:95) to give the title compound (0.0059 g, 4%) as a white solid.

Workup

  1. customand purified by ion-exchange (DOWEX™ 50WX2-100) resin
  2. washeluting with a solvent gradient of ammonia:water (5:95)

Sources & evidence

ORD record
ord-4d106ac2f13e4f9e9145e4847afd8525
Source dataset
uspto-grants-2006_05
Patent number
US07053122B2

Reaction notes

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