3-Bromopropionic acid → HCID 89377411, compound

HRID 1468573Notes

Reaction equation

HRID 1468573 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][C:5](=[O:7])[CH:6]=1.Br[CH2:9][CH2:10][C:11]([OH:13])=[O:12]>O1CCOCC1>[CH3:1][C:2]1[CH2:6][C:5](=[O:7])[N:4]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[N:3]=1

Participants

4

Reactant 2

HCID 115533-Bromopropionic acidHCID 198973125-Methyl-3H-pyrazol-3-one

Product 1

HCID 89377411HCID 89377411, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-methyl-pyrazol-5-one (5.7 g, 58.0 mmol) in anhydrous 1,4-dioxane was added 3-bromopropionic acid, and the resulting mixture was heated to reflux for 48 h.12 The reaction mixture was concentrated under reduced pressure, and the crude product was purified by column chromotography using 5-10% MeOH/DCM as an eluent to give 3j (22%) as a solid.13 mp: 210-215° C. (Lit. mp 178-180° C.); 1H NMR (400 MHz, CDCl3): δ 2.21 (s, 3H), 2.76 (m, 2H), 3.14 (s, 2H), 4.14 (m, 2H), 8.01 (brs, 1H); HRMS (m/z): [M−H]− calcd for C7H4N2O3, 169.0619; found, 169.0622.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 48 h
  3. concentration12 The reaction mixture was concentrated under reduced pressure
  4. customthe crude product was purified by column chromotography

Sources & evidence

ORD record
ord-85371d4e8ed847528cc3a12b83fb546c
Source dataset
uspto-grants-2015_04
Patent number
US09005670B2

Reaction notes

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