Nitric Acid → 3-Ethoxy-2-methyl-6-nitropyridine

HRID 128603

Reaction equation

HRID 128603 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([CH3:10])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]1[C:5]([CH3:10])=[N:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 128750153-Ethoxy-2-methylpyridine

Product 1

HCID 128750163-Ethoxy-2-methyl-6-nitropyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

3-Ethoxy-2-methylpyridine (132.5 g) was added dropwise to concentrated sulphuric acid (530 ml) with stirring and cooling to keep the mixture below 10° C. A mixture of concentrated nitric acid (81 ml) and concentrated sulphuric acid (97 ml) was added dropwise over 4 hours, keeping the temperature below 5° C. The reaction mixture was allowed to warm up slowly to ambient temperature and then added in portions to ice/water (2.5 l). The solid was collected by filtration, washed with water and dried under vacuum at 50° C. to give 3-ethoxy-2-methyl-6-nitropyridine, m.p. 82°-84° C.

Workup

  1. temperaturecooling
  2. customthe mixture below 10° C
  3. additionwas added dropwise over 4 hours
  4. customthe temperature below 5° C
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-c3a8131bb97e458d8ebfefbe5a1eecc9
Source dataset
uspto-grants-1995_11
Patent number
US05464781

Linked notes

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