Ethanol → Ethyl 6-amino-5-nitropyridine-3-carboxylate

HRID 1644586Notes

Reaction equation

HRID 1644586 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([O:8][CH2:19][CH3:20])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2718816-Amino-5-nitronicotinic acid

Product 1

HCID 22387769Ethyl 6-amino-5-nitropyridine-3-carboxylateYield 73%

Procedure

A solution of 6-amino-5-nitronicotinic acid (10 g) and concentrated sulfuric acid (20 ml) in ethanol (250 ml) was heated under reflux for 18 hr. The reaction mixture was concentrated, diluted with water and adjusted with sodium hydrogencarbonate to pH 8. The precipitated crystals were collected by filtration and washed with water to give the title compound (8.5 g, yield 73%) as yellow crystals. purity 84%. M+H: 212.

Workup

  1. temperatureunder reflux for 18 hr
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-0a933b6db7ba42edaa12b86b107ed684
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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