2-Nitropropane → 5-formyl-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester

HRID 280464Notes

Reaction equation

HRID 280464 reaction equation
[Na].[N+](C(C)C)([O-])=[O:3].Br[CH2:9][C:10]1[N:14]([C:15]([CH3:18])([CH3:17])[CH3:16])[N:13]=[CH:12][C:11]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[CH:9]([C:10]1[N:14]([C:15]([CH3:18])([CH3:17])[CH3:16])[N:13]=[CH:12][C:11]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:3]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 13654178HCID 13654178, compound

Product 1

HCID 136541795-formyl-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl esterYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This reaction was conducted in accordance with the procedure described by H. B. Hass and M. L. Bender in J. Am. Chem. Soc., 71, 1767 (1949). Sodium (1.6 grams, 0.07 mole) was dissolved in 50 ml of absolute ethanol. Subsequently, 2-nitropropane (8.1 grams, 0.09 mole) and 5-(bromomethyl)-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester (20 grams, 0.07 mole) were added. The resulting reaction mixture was refluxed for two hours, then cooled and the solvent removed in vacuo. The residue was taken up in ether, washed with water, washed with 1N sodium hydroxide, washed with saturated brine, and dried using sodium sulfate and filter paper. The solvent was removed in vacuo and the residue was distilled at 110° C. at 1.6 mm mercury pressure, yielding 11 grams of the 5-formyl-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for two hours
  3. temperaturecooled
  4. customthe solvent removed in vacuo
  5. washwashed with water
  6. washwashed with 1N sodium hydroxide
  7. washwashed with saturated brine
  8. customdried
  9. filtrationfilter paper
  10. customThe solvent was removed in vacuo
  11. distillationthe residue was distilled at 110° C. at 1.6 mm mercury pressure

Sources & evidence

ORD record
ord-3588ce5e332e4b7cb471594914e4dd26
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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