HCID 45417002, compound → HCID 86675893, compound

HRID 710015Notes

Reaction equation

HRID 710015 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:15][CH2:14]1)[C:7]([OH:9])=[O:8])([O-])=O>CCO.CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N:13]1[CH2:14][CH2:15][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:17][CH2:18]1)[C:7]([OH:9])=[O:8].[NH2:1][C:4]1[CH:5]=[CH:6][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 45417002HCID 45417002, compound

Product 1

HCID 86675893HCID 86675893, compoundYield 143.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

In a mixture of EtOH (100 mL) and MeOH (100 mL) compound acid 3-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid (2.0 g, 5.86 mmol) was dissolved and evacuated for 5 min. This was added to a 3-necked flask containing Pd/C (0.2 g of 5 wt %) under nitrogen. The reaction mixture was evacuated and nitrogen purged two times and stirred under a balloon of hydrogen for 4 h. LC-MS indicated the completion of reaction and the contents were evacuated and nitrogen purged and filtered through celite, and concentrated to give the aniline 3-amino-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid (1.7 g, 94%).

Workup

  1. dissolutionwas dissolved
  2. customevacuated for 5 min
  3. additionThis was added to a 3-necked flask
  4. additioncontaining Pd/C (0.2 g of 5 wt %) under nitrogen
  5. customThe reaction mixture was evacuated
  6. customnitrogen purged two times
  7. customthe completion of reaction
  8. customthe contents were evacuated
  9. customnitrogen purged
  10. filtrationfiltered through celite
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-53db5cf26d294fbb9228455bfd5641e1
Source dataset
uspto-grants-2015_11
Patent number
US09181226B2

Reaction notes

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