(4-Methoxyphenyl)hydrazine → HCID 178492077, compound

HRID 1244540Notes

Reaction equation

HRID 1244540 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][CH:23]([C:26](=[O:31])C(Cl)(Cl)Cl)[C:22](=O)[C:21]2=[O:33])=[CH:16][CH:15]=1)([O-:13])=[O:12]>CO.C(O)(=O)C>[OH:31][C:26]1[C:23]2[CH2:24][CH2:25][N:20]([C:17]3[CH:18]=[CH:19][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=3)[C:21](=[O:33])[C:22]=2[N:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 77023(4-Methoxyphenyl)hydrazineHCID 21919818HCID 21919818, compound

Product 1

HCID 178492077HCID 178492077, compound

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

Condensation of 4-methoxyphenylhydrazine with 1-(4-nitro-phenyl)-4-(2,2,2-trichloro-acetyl)-piperidine-2,3-dione in refluxing methanol-acetic acid media afforded 3-hydroxy-1-(4-methoxy-phenyl)-6-(4-nitro-phenyl)-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one. Treatment of this intermediate with NaH and isopropyliodide afforded the corresponding 3-isopropoxy pyrazolo intermediate which was subjected to the same experimental protocol as described for Example 3 to afford the title compound. ESI mass spectrum 460 (M+H)+.

Sources & evidence

ORD record
ord-1b3c136883874a1599a5653dbf21f4e3
Source dataset
uspto-grants-2006_10
Patent number
US07122557B2

Reaction notes

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