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

HRID 557702Notes

Reaction equation

HRID 557702 reaction equation
C[O:2][C:3](=[O:23])[C:4]([CH3:22])([CH3:21])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)[CH2:8][CH2:7]1.CO.[OH-].[Na+]>O1CCCC1>[CH3:21][C:4]([CH3:22])([CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)[CH2:10][CH2:11]1)[C:3]([OH:23])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 667381462,2-dimethyl-3-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid methyl ester

Product 1

HCID 667381622,2-dimethyl-3-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,2-Dimethyl-3-(5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-propionic acid methyl ester (199 mg, 0.62 mmol) from above was dissolved in tetrahydrofuran (2 mL). Then methanol (4 mL) and sodium hydroxide solution (1N, 2 mL) were added. The mixture was stirred and refluxed for 8 hrs. Solvents were evaporated and the residue was dissolved in hot methanol. The solution was cooled to room temperature and hydrochloric acid (1N, 2 mL) was added. The resulting mixture was cooled in an ice bath and the solid was filtered and washed with water. The solid was dried in air to give 2,2-dimethyl-3-(5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-propionic acid (181.5 mg). The NMR spectrum obtained on the sample is compatible with its structure. LC-MS calcd for C15H21N3O4 (m/e) 307.34, obsd 308.1 (M+H).

Workup

  1. temperaturerefluxed for 8 hrs
  2. customSolvents were evaporated
  3. dissolutionthe residue was dissolved in hot methanol
  4. additionhydrochloric acid (1N, 2 mL) was added
  5. temperatureThe resulting mixture was cooled in an ice bath
  6. filtrationthe solid was filtered
  7. washwashed with water
  8. customThe solid was dried in air

Sources & evidence

ORD record
ord-0277a800ae834c52acfaec028f71b08f
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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