Tetrahydrofuran → 6-(4-Aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile

HRID 81065ノート

反応式

HRID 81065 の反応式
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[N:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=2)[CH:3]=1.[Cl-].[NH4+].C1COCC1>[Zn].CO>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([C:8]#[N:9])=[C:6]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:12][CH:11]=3)[N:5]=2)=[CH:28][CH:27]=1

参加物

6

反応物 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 669270004-Chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile

生成物 1

HCID 669269446-(4-Aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile収率 40.2%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

A mixture of 4-chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile (136.3 mg, 0.319 mmol), zinc dust (312 mg, 4.78 mmol), ammonium chloride (256 mg, 4.78 mmol), THF (3 mL) and methanol (3 mL) was stirred at room temperature for 15 min, and filtered. The filtrate was concentrated and partitioned with dichloromethane and saturated sodium bicarbonate. The organic layer was separated and concentrated. Silica gel chromatography, eluting with 0-40% ethyl acetate in hexanes, gave pure 6-(4-aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile as yellow solid (51 mg). 1H NMR (400 MHz, CDCl3) δ ppm 7.96-8.04 (4H, m), 7.70 (1H, s), 7.40 (2H, t, J=8.03 Hz), 7.18 (1H, t, J=7.40 Hz), 7.08-7.14 (4H, m), 6.76 (2H, δ, J=8.78 Hz), 4.04 (2H, s); MS (ES+) m/z: 398 (M+H); LC retention time: 4.551 min (analytical HPLC Method A). Additional impure product was also obtained from the chromatography (48.1 mg).

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompartitioned with dichloromethane and saturated sodium bicarbonate
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. washSilica gel chromatography, eluting with 0-40% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-509b039825f144e680a55a26c46d6e35
出典データセット
uspto-grants-2014_09
特許番号
US08846673B2

反応ノート

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