HCID 68443943, compound → HCID 68445902, compound

HRID 388972Notes

Reaction equation

HRID 388972 reaction equation
[NH2:1][C:2]1[C:19]([N+:20]([O-])=O)=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[O:7])=[C:4]([Cl:23])[CH:3]=1>C(O)C.CC(O)=O.[Fe]>[NH2:1][C:2]1[C:19]([NH2:20])=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[O:7])=[C:4]([Cl:23])[CH:3]=1

Participants

5

Reactant 1

HCID 68443943HCID 68443943, compound

Product 1

HCID 68445902HCID 68445902, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 4-amino-2-chloro-N-(1H-indazol-6-yl)-5-nitrobenzamide (2 mmol; see Example 154) in ethanol (5 mL) and AcOH (1 mL) was added with iron powder (10 mmol). The reaction mixture was then heated to reflux for 6 h. The contents were cooled to RT, filtered through Celite pad, and the pad was washed with ethanol. The filtrates were combined and concentrated in vacuo. The residue obtained was purified on a silica gel column chromatography using MeOH/DCM as eluent to afford 4,5-diamino-2-chloro-N-(1H-indazol-6-yl)benzamide.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 6 h
  3. filtrationfiltered through Celite pad
  4. washthe pad was washed with ethanol
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas purified on a silica gel column chromatography

Sources & evidence

ORD record
ord-68d2418e88c74cb78d6412e53afddb93
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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