Water → 2-(5-Amino-pyridin-2-yl)-malonic acid dibenzyl ester

HRID 858066Notes

Reaction equation

HRID 858066 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[CH:10]([C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][N:22]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.O.[Cl-].[NH4+]>CO.[Zn]>[CH2:1]([O:8][C:9](=[O:30])[CH:10]([C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][N:22]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 69115439Dibenzyl 5-nitro-2-pyridylmalonate

Product 1

HCID 691148292-(5-Amino-pyridin-2-yl)-malonic acid dibenzyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(5-nitro-pyridin-2-yl)-malonic acid dibenzyl ester in a mixture of methanol, tetrahydrofuran, and water was treated with ammonium chloride (25 eq.) and zinc dust (>10 micron,10 eq.). The mixture was stirred at 25° C. for 40 min. At this time, the reaction was filtered through celite. The filtrate was concentrated in vacuo. The aqueous residue was extracted with ethyl acetate. The organics were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2-(5-amino-pyridin-2-yl)-malonic acid dibenzyl ester as a yellow viscous oil (89%); LRMS for C22H20N2O4 (M+H)+ at m/z=377.

Workup

  1. filtrationAt this time, the reaction was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. extractionThe aqueous residue was extracted with ethyl acetate
  4. washThe organics were washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a24a2b9009341c9976e16d3abb5ee36
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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