HCID 13147347, compound → HCID 59447939, compound

HRID 1916299Notes

Reaction equation

HRID 1916299 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:15]#[N:16])[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[N+:12]([O-])=O)[CH3:2]>C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4]([C:5]1[C:6]2[C:7](=[CH:8][N:9]=[CH:10][CH:11]=2)[NH:12][C:15]=1[NH2:16])=[O:17])[CH3:2]

Participants

4

Reactant 1

HCID 13147347HCID 13147347, compound

Product 1

HCID 59447939HCID 59447939, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A solution of cyano-(3-nitro-pyridin-4-yl)-acetic acid ethyl ester (2.50 g, 10.6 mmol) in 20 mL acetic acid was heated to 80° C. under nitrogen. Zinc powder was added in 500 mg portions over 20 minutes and the reaction mixture was then heated to 95° C. and stirred for 1 hour. Upon cooling, the insoluble material was removed by filtration and washed with acetic acid. The resulting filtrate was concentrated in vacuo and the residue treated with saturated sodium bicarbonate solution to give a light brown solid which was collected by filtration and dried in vacuo to a constant weight to give the title compound (2.02 g, 93%). 1H NMR (DMSO) δ 11.0 (1H, s, br), 8.31 (1H, br), 8.0 (1H, br), 7.41 (1H, d, J=4.7), 7.0 (2H, br s), 4.23 (2H, q, J=7.1), 1.32 (3H, t, J=7.1).

Workup

  1. temperatureUpon cooling
  2. customthe insoluble material was removed by filtration
  3. washwashed with acetic acid
  4. concentrationThe resulting filtrate was concentrated in vacuo
  5. additionthe residue treated with saturated sodium bicarbonate solution
  6. customto give a light brown solid which
  7. filtrationwas collected by filtration
  8. customdried in vacuo to a constant weight

Sources & evidence

ORD record
ord-5927bc776c28487b8e23a451ee460c46
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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