1-benzyl-4-nitro-1H-indazole → 4-Nitroindazole

HRID 614840Notes

Reaction equation

HRID 614840 reaction equation
C([N:8]1[C:16]2[C:11](=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9]1)C1C=CC=CC=1.C(N1C=C2C(C=CC=C2[N+]([O-])=O)=N1)C1C=CC=CC=1>>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[N:9][NH:8]2)([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 213272561-benzyl-4-nitro-1H-indazoleHCID 21327263HCID 21327263, compound

Product 1

HCID 180574-Nitroindazole

Procedure

The isomeric mixture of 1-benzyl-4-nitroindazole and 2-benzyl-4-nitroindazole obtained by the benzylation of 4-nitroindazole is reduced with hydrazine and Raney nickel in methanol and subsequently heated with excess sodium hydrogen sulphite in water. The 1-benzyl-4-aminoindazole (m.p. 73°-75° C.) thereby remains undissolved. Upon acidifying the solution, 2-benzyl-4-hydroxyindazole precipitates out and is obtained in the form of colorless crystals; m.p. 172°-174° C.

Sources & evidence

ORD record
ord-1ed06d394fe24e75a70c5eb395023faf
Source dataset
uspto-grants-1979_03
Patent number
US04146630

Reaction notes

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