Hydrochloric Acid → 3-Nitro-4-(propylamino)benzoic acid

HRID 74259Notes

Reaction equation

HRID 74259 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].[CH2:20]([NH2:23])[CH2:21][CH3:22].Cl>C(O)C.C(O)(=O)C.O>[N+:11]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[NH:23][CH2:20][CH2:21][CH3:22])[C:6]([OH:8])=[O:7])([O-:13])=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7852PropylamineHCID 11430Potassium CarbonateHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 117155563-Nitro-4-(propylamino)benzoic acidYield 80.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 4-fluoro-3-nitrobenzoic acid (2.0 g, 10.8 mmol) in ethanol (20 mL) was added potassium carbonate (2.34 mg, 16.2 mmol) and propylamine (1.27 g, 21.6 mmol), and this was heated to reflux for 4 hours. After the reaction was complete, this was cooled to room temperature, and water was added, this was adjusted to pH 5 with 10% hydrochloric acid and acetic acid, and after the precipitated crystals were filtered and washed with water, they were dried to yield the title compound (1.94 g, 80% yield).

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 4 hours
  3. filtrationafter the precipitated crystals were filtered
  4. washwashed with water, they
  5. customwere dried

Sources & evidence

ORD record
ord-b11824998cb14d9e824caaa0d4217f84
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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