Ammonium Chloride → HCID 71680392, compound

HRID 1469726Notes

Reaction equation

HRID 1469726 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][N:10]=[C:9]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[F:24][C:21]([F:22])([F:23])[C:17]1[CH:16]=[C:15]([NH:14][C:9]2[C:8]3[C:13](=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=3)[N:12]=[CH:11][N:10]=2)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 716778818-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine

Product 1

HCID 71680392HCID 71680392, compoundYield 77.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 8-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine (500 mg, 1.49 mmol) and iron powder (834 mg, 14.9 mmol) in EtOH (10 mL) was added a solution of NH4Cl (649 mg, 11.92 mmol) in water (3 mL) and the reaction mixture was heated at reflux for 2 h. Then the reaction mixture was cooled to rt and filtered. The filtrate was concentrated and the concentrate was dissolved in CHCl3. The organic layer was washed with an aq. saturated solution of NaHCO3 and brine. The organic layer was dried, filtered and concentrated to afford 350 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 9.74 (br s, 1H), 8.59 (s, 1H), 8.38 (s, 1H), 8.26 (d, J=7.8 Hz, 1H), 7.64-7.59 (m, 2H), 7.45-7.42 (d, J=7.5 Hz, 1H), 7.37-7.32 (t, J=8.0 Hz, 1H), 7.00-6.98 (d, J=7.8 Hz, 1H), 5.91 (br s, 2H); MS (m/z): 305.27 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe concentrate was dissolved in CHCl3
  6. washThe organic layer was washed with an aq. saturated solution of NaHCO3 and brine
  7. customThe organic layer was dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b28efa1fc7734105ae2298dac569693e
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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