4-(p-Tolyloxy)aniline → HCID 68512931, 화합물

HRID 1716294노트

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HRID 1716294 반응식
[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

참가 물질

5

반응물 3

HCID 945194-(p-Tolyloxy)anilineHCID 15164035-Bromo-2-methoxypyridine-3-carbaldehydeHCID 4311764Sodium borohydride2회

생성물 1

HCID 68512931HCID 68512931, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-6a3c5efd0a644e5d901c45ad6e36b609
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803793B2

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