Hydrochloric Acid → 2-Methyl-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid

HRID 1481868

Reaction equation

HRID 1481868 reaction equation
F[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:14])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[C:23]1([CH3:35])[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.Cl>CN(C=O)C>[CH3:14][C:4]1[CH:3]=[C:2]([N:32]2[CH2:33][CH2:34][N:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH3:35])[CH2:30][CH2:31]2)[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 919641-(o-Tolyl)piperazine dihydrochlorideHCID 223131014-Fluoro-2-methyl-5-nitrobenzoic acid

Product 1

HCID 896906482-Methyl-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-fluoro-2-methyl-5-nitro-benzoic acid (5.0 g, 25.10 mmol) in anhydrous DMF (100 mL), potassium carbonate (10.4 g, 75.3 mmol) was added under N2 atmosphere followed by 1-o-tolyl-piperazine 2 HCl (8.13 g, 32.6 mmol). The reaction mixture was allowed to stir at room temperature overnight. The progress of the reaction was checked by TLC, upon completion of the reaction, solvent was removed in vacuo. The residue obtained was acidified with conc. HCl (≈pH=2-3). Yellow solid obtained was filtered and washed with water (3×75 mL), diethyl ether and dried under vacuo to obtain the pure product 2-methyl-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid. Yield (6.5 g, 73%; and yellow solid).

Workup

  1. customThe progress of the reaction was checked by TLC, upon completion of the reaction, solvent
  2. customwas removed in vacuo
  3. customThe residue obtained
  4. customYellow solid obtained
  5. filtrationwas filtered
  6. washwashed with water (3×75 mL), diethyl ether
  7. customdried under vacuo

Sources & evidence

ORD record
ord-ed984582d8f44b28aed168943abd906e
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Linked notes

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