Sodium Hydroxide → 2-methyl-2-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid

HRID 1641773Notes

Reaction equation

C([O:3][C:4](=[O:23])[C:5]([CH3:22])([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][N:14]=2)[CH2:9][CH2:8]1)[CH3:6])C.[OH-].[Na+]>O1CCCC1.CO>[CH3:22][C:5]([CH:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][N:14]=2)[CH2:11][CH2:12]1)([CH3:6])[C:4]([OH:23])=[O:3]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 2-methyl-2-(5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-propionic acid ethyl ester (321 mg, 1.0 mmol) in tetrahydrofuran (2 mL) and methanol (6 mL) was added sodium hydroxide solution (1N, 2 mL). The mixture was heated in a microwave at 140° C. for 1.5 hr. The mixture was evaporated and the residue was dissolved in hot methanol and water. The clear solution was then acidified with 1N hydrochloric acid (2.5 mL). The resulting pale yellow precipitate was filtered and dried to give 2-methyl-2-(5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-propionic acid (210 mg). LC-MS calcd. for C14H19N3O4 (m/e) 293.1, obsd 294.1

Workup

customThe mixture was evaporated
dissolutionthe residue was dissolved in hot methanol
filtrationThe resulting pale yellow precipitate was filtered
customdried

Sources & evidence

ORD record: ord-06882f82f9cf49449ffb9719b4c53d78
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08115011B2

Reaction notes

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