Ammonia → HCID 592440, compound

HRID 2228916Notes

Reaction equation

HRID 2228916 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=O)[CH:4]=[N:3]1.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12].N1CCCCC1.N.Cl>O.N1C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=[CH:10][C:11]([OH:13])=[O:12])[CH:4]=[N:3]1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 5731171-Methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 592440HCID 592440, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-methylpyrazole-4-carboxaldehyde (made as in reference 15) (18.1 g), malonic acid (17.1 g), pyridine (15 ml) and piperidine (0.2 ml) was heated to 100° C. for 1 hour. After cooling, water was added, followed by aqueous ammonia to obtain a clear solution, which was acidified to pH5 with hydrochloric acid. The resulting solid was filtered off, washed with water and dried to obtain 3-(1-methylpyrazol-4-yl)acrylic acid (18.9 g). 1H-NMR (d6-DMSO) δ 3.83 (3H, s), 6.18 (1H, d), 7.44 (1H, d), 7.83 (1H, s), 8.07 (1H, s). (APCI) M+H=153. C7H8N2O2 requires 152.

Workup

  1. temperatureAfter cooling
  2. customto obtain a clear solution, which
  3. filtrationThe resulting solid was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a0a3d989b3364f21b1d453c5259ef799
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

Loading…