HCID 136392270, compound → HCID 69024323, compound

HRID 1393897Notes

Reaction equation

HRID 1393897 reaction equation
[CH2:1]([O:3][C:4](=[O:28])/[C:5](/O)=[CH:6]/[C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][N:10]=[C:9]([N:16]2[CH2:21][CH2:20][N:19]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:18][CH2:17]2)[CH:8]=1)[CH3:2]>C(O)(=O)C.[Fe]>[CH2:1]([O:3][C:4]([C:5]1[NH:13][C:12]2=[CH:11][N:10]=[C:9]([N:16]3[CH2:21][CH2:20][N:19]([CH:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[CH2:18][CH2:17]3)[CH:8]=[C:7]2[CH:6]=1)=[O:28])[CH3:2]

Participants

4

Reactant 1

HCID 136392270HCID 136392270, compound

Product 1

HCID 69024323HCID 69024323, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

(Z)-3-[2-(4-Cyclopentyl-piperazin-1-yl)-5-nitro-pyridin-4-yl]-2-hydroxy-acrylic acid ethyl ester was reacted with 0.47 g iron powder in 40 mL acetic acid for 6 h at 80° C. After evaporation of all volatiles the residue was taken up in water and extracted with DCM. The combined organic layers were dried with MgSO4 and evaporated to dryness. Purification on silica eluting with a gradient mixture of n-heptan/ethyl acetate/0.1% NEt3 yielded after evaporation of the product fractions 0.65 g (23% from 2-chloro-4-methyl-5-nitropyridine) of the title compound as light brown solid.

Workup

  1. customAfter evaporation of all volatiles the residue
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried with MgSO4
  4. customevaporated to dryness
  5. customPurification on silica eluting
  6. additionwith a gradient mixture of n-heptan/ethyl acetate/0.1% NEt3
  7. customyielded
  8. customafter evaporation of the product fractions 0.65 g (23% from 2-chloro-4-methyl-5-nitropyridine) of the title compound as light brown solid

Sources & evidence

ORD record
ord-8b1ef578888043e4b67a967a97f6c9d3
Source dataset
uspto-grants-2008_03
Patent number
US07348323B2

Reaction notes

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