Ammonium Chloride → 4-(3-(Trifluoromethyl)phenoxy)quinolin-8-amine

HRID 1469735ノート

反応式

HRID 1469735 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[O: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]([CH:20]=[CH:19][CH:18]=1)[O:14][C:9]1[C:8]2[C:13](=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=2)[N:12]=[CH:11][CH:10]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 866922328-Nitro-4-(3-(trifluoromethyl)phenoxy)quinoline

生成物 1

HCID 716780474-(3-(Trifluoromethyl)phenoxy)quinolin-8-amine収率 82.2%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a suspension of 8-nitro-4-(3-(trifluoromethyl)phenoxy)quinoline (200 mg, 0.60 mmol) and iron powder (267 mg, 4.77 mmol) in EtOH (3 mL) was added a solution of NH4Cl (312 mg, 5.89 mmol) in water (2 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 separated, dried, filtered and concentrated to afford 150 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.58 (d, J=4.8 Hz, 1H), 7.77-7.65 (m, 3H), 7.55 (d, J=7.8 Hz, 1H), 7.32 (m, 2H), 6.64 (m, 1H), 6.71 (d, J=4.8 Hz, 1H), 6.00 (br s, 2H); MS (m/z): 305.22 (M+H)+.

後処理

  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 separated
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-661d34a653f44903bbc1c0178e57c89d
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

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