Water → HCID 68607684, compound

HRID 2171229Notes

Reaction equation

HRID 2171229 reaction equation
[Cl-].[NH4+].O.[CH3:4][O:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9]1.[CH3:20][O:21][CH2:22][CH2:23][N:24]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][CH:29]=[C:30]2[N+:33]([O-])=O)=[N:25]1>[Fe].C(OCC)(=O)C.CCO>[CH3:4][O:5][CH2:6][CH2:7][N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[CH:10]=[N:9]1.[CH3:20][O:21][CH2:22][CH2:23][N:24]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][CH:29]=[C:30]2[NH2:33])=[N:25]1

Participants

9

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 89537356HCID 89537356, compoundHCID 89538293HCID 89538293, compound

Product 2

HCID 68607684HCID 68607684, compoundHCID 68608031HCID 68608031, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (170 mg), ammonium chloride (160 mg), and water (3 ml) were added to an EtOH (10 ml) solution containing the mixture of 1-(2-methoxyethyl)-4-nitro-1H-indazole and 2-(2-methoxyethyl)-4-nitro-2H-indazole obtained in the 1st step, followed by stirring at 80° C. for 2 hours. Ethyl acetate was added to the reaction solution, insoluble matter was removed by filtration, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel-alumina column chromatography. 1-(2-methoxyethyl)-1H-indazol-4-amine (49 mg) and 2-(2-methoxyethyl)-2H-indazol-4-amine (40 mg) were thus obtained.

Workup

  1. additioncontaining
  2. customobtained in the 1st step
  3. customwas removed by filtration
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel-alumina column chromatography

Sources & evidence

ORD record
ord-355c1e5dd48a4c1796419129878f2da8
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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