Water → methyl 4-nitro-1H-indazole-1-carboxylate

HRID 887226Notes

Reaction equation

HRID 887226 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[N:9][NH:10]2)([O-:5])=[O:4].[CH3:15][O:16][C:17](Cl)=[O:18].O>CN(C=O)C>[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[N:9][N:10]2[C:17]([O:16][CH3:15])=[O:18])([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 180574-NitroindazoleHCID 24758Sodium hydride

Product 1

HCID 22032604methyl 4-nitro-1H-indazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.3 g, 12.5 mmol) suspended in DMF (5 mL) at 0° C. was treated with 4-nitro-1H-indazole (1.33 g, 10 mmol). After stirring at room temperature for 1 hour, the mixture was treated with methylchloroformate (0.9 mL). After stirring at room temperature for 3 hours, the mixture was carefully treated with water and filtered to provide the title compound (1.2 g). 1H NMR (300 MHz, DMSO-d6) δ 4.19 (s, 3H), 7.9 (t, 1H), 8.38 (d, 1H), 8.62 (d, 1H), 8.85 (s, 1H).

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-5ad1cd084f9d4af196a2ee70f4015f00
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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