Hydrochloric Acid → Diethyl 5-amino-2-chloro-6-methylpyridine-3,4-dicarboxylate

HRID 37477Notes

Reaction equation

HRID 37477 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([N+:18]([O-])=O)=[C:4]([CH3:21])[N:3]=1.Cl>C(O)C>[NH2:18][C:5]1[C:4]([CH3:21])=[N:3][C:2]([Cl:1])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 199355842-Chloro-3,4-diethoxycarbonyl-6-methyl-5-nitropyridine

Product 1

HCID 15289693Diethyl 5-amino-2-chloro-6-methylpyridine-3,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 15 ml of ethanol was dissolved 1.2 g of 2-chloro-3,4-diethoxycarbonyl-6-methyl-5-nitropyridine, whereto 1.9 g (9 eq.) of reduced iron was added, followed by adding dropwise 7.1 ml of hydrochloric acid. The mixture was stirred at room temperature for 30 minutes. After the solvent was distilled off, the residue was neutralized with sodium hydrogencarbonate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried. The solvent was distilled off to give an oily product.

Workup

  1. additionwas added
  2. distillationAfter the solvent was distilled off
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. customdried
  6. distillationThe solvent was distilled off
  7. customto give an oily product

Sources & evidence

ORD record
ord-85212bf9fa35470e9ef24fe3284c0ef7
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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