Acetic Acid → (3,5-Dimethyl-4-nitropyridin-2-yl)methanol

HRID 380728Notes

Reaction equation

HRID 380728 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[N+:8]([C:11]1[C:16](C)=[CH:15][N+:14]([O-])=[C:13](C)[C:12]=1[CH3:20])([O-:10])=[O:9].C(O)(=O)C.[OH-].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CO>[OH:7][CH2:5][C:6]1[C:16]([CH3:15])=[C:11]([N+:8]([O-:10])=[O:9])[C:12]([CH3:20])=[CH:13][N:14]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxide

Product 1

HCID 4049415(3,5-Dimethyl-4-nitropyridin-2-yl)methanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

151.3 gms (1.4833 mole) of acetic anhydride was added at 45-50° C. to a mixture of 90.0 gm (o.4595 moles) of 4-nitro-2,3,5-trimethylpyridine-N-oxide of formula-IV and 45.0 gms of acetic acid and heated to 85° C. and maintained at the temperature at 85-90° C. for 4 hrs. 75 ml of methanol was added to the reaction mixture at room temperature and distilled off acetic acid and methanol at temperature of 60-65° C. under vacuum to get an oil. 40% Sodium hydroxide solution (240 g) was added to the cooled oil at 0-5°°C. and stirred for 4 hrs. The crude product was obtained by extraction of the reaction mass with methylene chloride and distillation of the solvent. Pure 2-hydroxymethyl-3,5-dimethyl-4-nitropyridine of formula-II was obtained by re-crystallization of the crude material in toluene.

Workup

  1. temperaturemaintained at the temperature at 85-90° C. for 4 hrs
  2. distillationdistilled off acetic acid and methanol at temperature of 60-65° C. under vacuum
  3. customto get an oil

Sources & evidence

ORD record
ord-414fc1153b5c4c07ba3f064f3d577a68
Source dataset
uspto-grants-2001_10
Patent number
US06303787B1

Reaction notes

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