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

HRID 485096Notes

Reaction equation

HRID 485096 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 a dryness to give 2-[4-cyano-1,1-dicarbethoxybutyl]-3-nitro-5-methylpyridine (18.3 g) as a yellow oil.

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 a dryness

Sources & evidence

ORD record
ord-c0912b86b312495cbe4010e2b572e24e
Source dataset
uspto-grants-1985_08
Patent number
US04535163

Reaction notes

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