3-Amino-3-Oxopropanoic Acid → 2-Carbamoyl-3-(1-methyl-3-nitro-4-pyrazolyl)-acrylic acid

HRID 426942Notes

Reaction equation

HRID 426942 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=O)[C:4]([N+:9]([O-:11])=[O:10])=[N:3]1.[C:12]([NH2:18])(=[O:17])[CH2:13][C:14]([OH:16])=[O:15]>N1C=CC=CC=1>[C:12]([C:13](=[CH:7][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[N:3][N:2]([CH3:1])[CH:6]=1)[C:14]([OH:16])=[O:15])(=[O:17])[NH2:18]

Participants

4

Reactant 2

HCID 753673-Amino-3-Oxopropanoic AcidHCID 203889181-Methyl-3-nitro-1H-pyrazole-4-carbaldehyde

Product 1

HCID 544152332-Carbamoyl-3-(1-methyl-3-nitro-4-pyrazolyl)-acrylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

When the reaction of 1-methyl-3-nitropyrazole-4-aldehyde and malonic acid monoamide in pyridine is carried out at 70° C., then, as intermediate product, there can be isolated 2-carbamoyl-3-(1-methyl-3-nitro-4-pyrazolyl)-acrylic acid. For decarboxylation, 0.1 g. of this product is stirred in 1 ml. pyridine for 1.5 hours at a bath temperature of 120° C. The reaction mixture is then cooled, ice-cold semi-concentrated hydrochloric acid is added thereto and the precipitated crystals are filtered off with suction, washed with water and dried. There is obtained 0.02 g. 3-(1-methyl-3-nitropyrazolyl)-acrylamide.

Workup

  1. customis carried out at 70° C.

Sources & evidence

ORD record
ord-9beb59377af347ac9cf03284105a015b
Source dataset
uspto-grants-1979_10
Patent number
US04172136

Reaction notes

Loading…