Nitric Acid → 6-Chloro-2-pyridylmethyl nitrate

HRID 579720

Reaction equation

HRID 579720 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].C(OC(=O)C)(=O)C.O[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[N:15]=1.C(=O)([O-])[O-].[K+].[K+]>>[O:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[N:15]=1)[N+:1]([O-:4])=[O:3]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 182139(6-Chloropyridin-2-yl)methanol

Product 1

HCID 1461996-Chloro-2-pyridylmethyl nitrate

Procedure

Fuming nitric acid (1.57 ml) was added dropwise to acetic anhydride (3.54 ml) with stirring at 0° to 5° C. 2-Hydroxymethyl-6-chloropyridine (3.59 g) was added thereto. The resulting mixture was stirred for 20 minutes at 0° C. to 5° C. The resulting mixture was alkalized weakly with an aqueous potassium carbonate solution, extracted with chloroform, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was subjected to column chromatography on aluminum oxide (40 g) and eluted with toluene. The fractions containing the desired compound were concentrated under reduced pressure to give colorless viscous oil of 2-nitroxymethyl-6-chloropyridine (2.9 g).

Workup

  1. stirringThe resulting mixture was stirred for 20 minutes at 0° C. to 5° C
  2. extractionextracted with chloroform
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. washeluted with toluene
  8. additionThe fractions containing the desired compound
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-f535e02077c44014b2bb4eb7229d20aa
Source dataset
uspto-grants-1988_06
Patent number
US04749574

Linked notes

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