Pyruvic Acid → HCID 85847975, compound

HRID 859847Notes

Reaction equation

HRID 859847 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[C:13]([OH:18])(=[O:17])[C:14]([CH3:16])=O>Cl>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][N:10]=[C:14]([CH3:16])[C:13]([OH:18])=[O:17])=[CH:7][CH:8]=1

Participants

4

Procedure

4-Trifluoromethylphenyl hydrazine (8.40 g, 47.7 mmol) was suspended in 1 N hydrochloric acid (130 ml) and fully stirred with a mechanical stirrer to obtain a suspension. A aqueous solution (50 ml) of pyruvic acid (4.20 g, 47.7 mmol) was added to the suspension and vigorously stirred to a mixture. 6 hours later, the mixture was extracted with ethyl acetate and washed with a saturated brine. The washed mixture was dried on sodium sulfate and then filtered. The residue obtained by concentrating the resulting filtrate was washed with a mixed solvent of hexane and chloroform (1:1) to obtain 2-(4-trifluoromethylphenyl hydrazono) propionic acid (10.47 g, 42.52 mmol, 89%). mp 190–191° C.; 1H NMR (400 MHz, CDCl3) δ 2.19 (3H, s), 7.23 (2H, d), 7.60 (2H, d), 7.87 (1H, brs).

Workup

  1. customto obtain a suspension
  2. stirringvigorously stirred to a mixture
  3. extraction6 hours later, the mixture was extracted with ethyl acetate
  4. washwashed with a saturated brine
  5. customThe washed mixture was dried on sodium sulfate
  6. filtrationfiltered
  7. customThe residue obtained
  8. concentrationby concentrating the resulting filtrate
  9. washwas washed with a mixed solvent of hexane and chloroform (1:1)

Sources & evidence

ORD record
ord-fbe391bd5b01477d8d7ee2671e9dac45
Source dataset
uspto-grants-2006_12
Patent number
US07153815B2

Reaction notes

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