Hydrochloric Acid → 2-(1,3-Dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetic acid hydrochloride

HRID 571333Notes

Reaction equation

HRID 571333 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[CH:8][CH:9]=2)[C:4](=[O:19])[N:3]1[CH2:20][C:21]([O:23]C)=[O:22].[ClH:25]>C1COCC1>[ClH:25].[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[CH:8][CH:9]=2)[C:4](=[O:19])[N:3]1[CH2:20][C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86681748Methyl 2-(1,3-dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetate

Product 1

HCID 866817492-(1,3-Dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetic acid hydrochlorideYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(1,3-dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetate (56 mg, 0.172 mmol) in THF (3 ml), aqueous 6N HCl (2002 μL, 12.01 mmol) was added, and the reaction mixture was stirred for 16 hours at room temperature and then heated at 50° C. for 5 hours. The volatiles were removed under vacuum and the crude was dried yielding 2-(1,3-dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetic acid hydrochloride (54 mg, 0.155 mmol, 90% yield, MS/ESI+ 313.0 [MH]+).

Workup

  1. temperatureheated at 50° C. for 5 hours
  2. customThe volatiles were removed under vacuum
  3. customthe crude was dried

Sources & evidence

ORD record
ord-f62ee2c13e5a41139ef7b68bf9d1afcf
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

Loading…