Hydrochloric Acid → 4-((Tetrahydropyran-4-yl)amino)-3-nitrobenzoic acid

HRID 74157

Reaction equation

HRID 74157 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(N(CC)CC)C.[NH2:21][CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.NC1CCCCO1.Cl>C(O)C.O>[O:25]1[CH2:26][CH2:27][CH:22]([NH:21][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])[CH2:23][CH2:24]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 679874-Fluoro-3-nitrobenzoic acidHCID 4192234-AminotetrahydropyranHCID 14471248Oxan-2-amine

Product 1

HCID 436103324-((Tetrahydropyran-4-yl)amino)-3-nitrobenzoic acidYield 101.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Fluoro-3-nitrobenzoic acid (126.4 g, 0.68 mol) was dissolved in ethanol (880 mL). Triethylamine (82.6 g, 0.82 mol), 4-aminotetrahydropyran (82.7 g, 0.81 mol) were added in turn dropwise, and after the additions the reaction solution was heated to reflux. After refluxing for 5 h, triethylamine (8.3 g, 82 mmol), aminotetrahydropyran (8.3 g, 81 mmol) were added, and this was refluxed for a further 9 hours. After the reaction mixture was allowed to cool to room temperature, 2N HCl (880 mL) and water (880 mL) were added and after stirring for awhile, the solid obtained was filtered off. This was forced air-dried at 60° C. to yield the title compound (183.3 g, quant.) as a yellow solid.

Workup

  1. temperatureafter the additions the reaction solution was heated to reflux
  2. temperatureAfter refluxing for 5 h
  3. temperaturethis was refluxed for a further 9 hours
  4. customobtained
  5. filtrationwas filtered off
  6. customThis was forced air-dried at 60° C.

Sources & evidence

ORD record
ord-3d585bfc7faf417584411f9094ad5215
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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