5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde → HCID 19738222, compound

HRID 2255493Notes

Reaction equation

HRID 2255493 reaction equation
N1N[CH:3]=[C:4]2C=COC=12.Cl[C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:13]=[C:12]([CH3:21])[C:11]=1[CH:22]=O.C([CH:26]([OH:30])[C:27]([O-:29])=[O:28])C>>[CH3:21][C:12]1[C:11]2[CH:22]=[C:26]([C:27]([O:29][CH2:3][CH3:4])=[O:28])[O:30][C:10]=2[N:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:13]=1

Participants

4

Reactant 3

HCID 6130275-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde2×HCID 4071895Alpha-HydroxybutyrateHCID 178419847HCID 178419847, compound

Product 1

HCID 19738222HCID 19738222, compound

Procedure

Furo[2,3-c]pyrazole compounds were first synthesized by two of the present inventors, L. J. Haung and S. C. Kuo, and H. T. Li in an article published in J. Taiwan Pharm. Assoc. 31 (1), 47-55 (1979). Ethyl 3-methyl-1-phenylfuro[2,3-c]pyrazole-5-carboxylate (3) was synthesized in this article. As shown in the following Scheme 1, chloro-3-methyl-1-phenylpyrazole-4-carboxaldehyde (1) and ethylglycolate (2) were condensed to form ethyl 3-methyl-1-phenylfuro[2,3-c]pyrazole-5-carboxylate (3); or 5-hydroxy-3-methyl-1-phenylpyrazole-4-carboxal-dehyde acetate (4) was reacted with ethylbromoacetate (5) to obtain the ethyl 3-methyl-1-phenylfuro[2,3-c]pyrazole-5-carboxylate (3). The product produced by these two methods are very low in yield and stability. Therefore, only one furo[2,3-c]pyrazole compound (3) was synthesized and no further investigation was conducted in the above-mentioned article. ##STR1##

Workup

  1. customEthyl 3-methyl-1-phenylfuro[2,3-c]pyrazole-5-carboxylate (3) was synthesized in this article
  2. customcondensed

Sources & evidence

ORD record
ord-fb0d174c3bae431f8d80e265a307eb2c
Source dataset
uspto-grants-1993_08
Patent number
US05240947

Reaction notes

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