4-(p-Tolyloxy)aniline → HCID 68512931、化合物

HRID 1716294ノート

反応式

HRID 1716294 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:12]1([CH3:26])[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:25][C:22]2[CH:21]=[CH:20][C:19]([O:18][C:15]3[CH:16]=[CH:17][C:12]([CH3:26])=[CH:13][CH:14]=3)=[CH:24][CH:23]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 945194-(p-Tolyloxy)anilineHCID 15164035-Bromo-2-methoxypyridine-3-carbaldehydeHCID 4311764Sodium borohydride2 回

生成物 1

HCID 68512931HCID 68512931、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

A solution of 5-bromo-2-methoxy-pyridine-3-carbaldehyde (0.87 g, 4.03 mmol) in dry MeOH (15 mL) was treated with 4-p-tolyloxy-phenylamine (0.88 g, 4.43 mmol) and reflux for 2.5 h. The solution was cooled to 0° C. and treated slowly with NaBH4 (0.38 g, 10.1 mmol). The reaction stirred at room temperature overnight. Additional NaBH4 (0.38 g, 10.1 mmol) was added and the reaction was continued stirring for additional 6 h. The solvent was removed and the residue was partitioned between CH2Cl2 (20 mL) and water (10 mL). The organic portion was brought to the usual work-up to give a crude material. The product was yielded after chromatography purification (silica gel, 25% EtOAc/hexanes). MS (EI) 399, 401 (M+H)+.

後処理

  1. temperaturereflux for 2.5 h
  2. stirringthe reaction was continued stirring for additional 6 h
  3. customThe solvent was removed
  4. customthe residue was partitioned between CH2Cl2 (20 mL) and water (10 mL)

出典と根拠

ORDレコード
ord-6a3c5efd0a644e5d901c45ad6e36b609
出典データセット
uspto-grants-2010_09
特許番号
US07803793B2

反応ノート

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