Hydrochloric Acid → 5-Fluoroquinolin-7-amine

HRID 1621840Notes

Reaction equation

HRID 1621840 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[N:16]3)=[C:11]([F:19])[CH:10]=2)C=CC=CC=1.Cl>C1COCC1.C([O-])(O)=O.[Na+]>[F:19][C:11]1[CH:10]=[C:9]([NH2:8])[CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][CH:15]=[N:16]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86647070N-(Diphenylmethylene)-5-fluoroquinolin-7-amine

Product 1

HCID 666002875-Fluoroquinolin-7-amineYield 89.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of N-(diphenylmethylene)-5-fluoroquinolin-7-amine (185 mg, 0.566 mmol) and hydrochloric acid (1.132 mL, 1.132 mmol) in THF (5 mL) was stirred at room temperature for 3 h. The reaction mixture was diluted with saturated NaHCO3 (5 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow oil. The crude product was purified by silica gel chromatography eluting with 80% EtOAc/hexanes to give 5-fluoroquinolin-7-amine (82 mg, 0.506 mmol, 89% yield). 1H NMR (300 MHz, CDCl3) δ 4.02 (s, 2H) 7.11 (dd, J=9.65, 8.18 Hz, 1H) 7.29-7.40 (m, 1H) 7.45 (d, J=2.48 Hz, 1H) 7.76 (d, J=8.48 Hz, 1H) 8.53 (d, J=2.78 Hz, 1H). m/z (ESI, +ve ion) 163.1 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. extractionThe organic extract
  3. washwas washed with saturated NaCl (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material as a light-yellow oil
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 80% EtOAc/hexanes

Sources & evidence

ORD record
ord-968c1b404cb94a2caa25d1f54f2012e2
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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