Ammonium Chloride → N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine

HRID 1469726노트

반응식

HRID 1469726 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

HCID 71680392N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine수율 77.2%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-b28efa1fc7734105ae2298dac569693e
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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