Sulfuric Acid → HCID 20313017, compound

HRID 2420100Notes

Reaction equation

HRID 2420100 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[N+:23]([O-])([O-:25])=[O:24].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>>[N+:23]([C:5]1[CH:4]=[CH:3][C:2]([CH2:1][C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[N:12][CH:13]=2)=[CH:7][CH:6]=1)([O-:25])=[O:24]

Participants

5

Reactant 4

HCID 1118Sulfuric Acid2×HCID 10340Sodium CarbonateHCID 24268Sodium NitrateHCID 20313016HCID 20313016, compound

Product 1

HCID 20313017HCID 20313017, compound

Procedure

6.0 Grams of methyl 5-benzylpicolinate were dissolved in 20 ml. of concentrated sulfuric acid at room temperature. A solution of 2.7 g of sodium nitrate in 20 ml. of concentrated sulfuric acid was added dropwise thereto under cooling to keep internal temperature at 5° C. After three hours, the reaction solution was poured into ice-water and neutralized with sodium carbonate. After extraction with ethyl acetate, washing with water and drying, the solvent was distilled out. The residue was recrystallized from methanol to obtain 3.5 g of 172°-178° C.

Workup

  1. customat room temperature
  2. temperatureunder cooling
  3. customat 5° C
  4. extractionAfter extraction with ethyl acetate
  5. washwashing with water
  6. customdrying
  7. distillationthe solvent was distilled out
  8. customThe residue was recrystallized from methanol
  9. customto obtain 3.5 g of 172°-178° C.

Sources & evidence

ORD record
ord-afea6cd7f0d04875bb0aee4beb49d242
Source dataset
uspto-grants-1978_08
Patent number
US04109000

Reaction notes

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