2-Chloro-5-methyl-3-nitropyridine → 2-[4-Cyano-1,1-dicarbethoxybutyl]-3-nitro-5-methylpyridine

HRID 326084Notes

Reaction equation

HRID 326084 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][N:3]=1.[CH2:12]([O:14][C:15](=[O:27])[CH:16]([CH2:22][CH2:23][CH2:24][C:25]#[N:26])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:13]>>[C:25]([CH2:24][CH2:23][CH2:22][C:16]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][N:3]=1)([C:15]([O:14][CH2:12][CH3:13])=[O:27])[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:26]

Participants

3

Reactant 2

HCID 8183002-Chloro-5-methyl-3-nitropyridineHCID 3641060Diethyl 2-(3-cyanopropyl)malonate

Product 1

HCID 202714572-[4-Cyano-1,1-dicarbethoxybutyl]-3-nitro-5-methylpyridine

Procedure

2-Chloro-5-methyl-3-nitro-pyridine (20 g) was reacted with 2-(3-cyanopropyl)malonic acid diethyl ester under conditions analogous to those in Example 1(a). The reaction mixture was partitioned between water and chloroform, the chloroform extract was dried, treated with charcoal and filtered through a silica bed and then evaporated to dryness to give 2-[4-cyano-1,1-dicarbethoxybutyl]-3-nitro-5-methylpyridine (18.3 g) as a yellow oil. N.M.R. (CDCl3) assignment, δ(p.p.m.), multiplicity; CO2CH2CH3 ×2, 1.2, t; --CH2CH2CH2CN, 1.3-2.0, m; --CH2CN, 2.37, m; 5-methylpyridyl, 2.49, s; CO2CH2CH3 ×2, 4.19, q; 4-pyridyl proton 8.17, m; 6-pyridyl proton, 8.57, m;

Workup

  1. customThe reaction mixture was partitioned between water and chloroform
  2. extractionthe chloroform extract
  3. customwas dried
  4. additiontreated with charcoal
  5. filtrationfiltered through a silica bed
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-17291da19acb43028f638342ca7ce06d
Source dataset
uspto-grants-1984_04
Patent number
US04444772

Reaction notes

Loading…