Quinoline → 2-Amino-4-hydroxy-3-methylbenzonitrile

HRID 579672노트

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HRID 579672 반응식
[CH2:1]([N:8]1C(=O)C2=CC=CC=C2C1=O)CCCCC=C.[OH-:19].[Na+].[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=CC=1>>[NH2:21][C:30]1[C:25]([CH3:24])=[C:26]([OH:19])[CH:27]=[CH:28][C:29]=1[C:1]#[N:8]

참가 물질

4

반응물 3

HCID 7047QuinolineHCID 14798Sodium HydroxideHCID 53236045N-(hept-6-enyl)phthalimide

생성물 1

HCID 134647162-Amino-4-hydroxy-3-methylbenzonitrile수율 82%

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온도
170 °C

실험 절차

A mixture of compound 75 (19 g, 0.1 mol) in quinoline (50 mL) was heated to 170° C. for 2 h (until effervescence ceased). The reaction mixture was cooled to RT and aqueous NaOH solution was added (1M, 500 mL) followed by pet. ether (500 mL). The reaction mixture was stirred for 15 min and the aqueous layer was separated. The aqueous layer was further washed with pet. ether (2×300 mL) to remove quinoline completely. The aqueous layer was acidified with 1.5N HCl to pH=5, the solid was filtered off and dried under vacuum. The obtained solid was further washed with 5% ethyl acetate in pet. ether to give pure title compound (12 g, 82%).

후처리

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe aqueous layer was separated
  3. washThe aqueous layer was further washed with pet. ether (2×300 mL)
  4. customto remove quinoline completely
  5. filtrationthe solid was filtered off
  6. customdried under vacuum
  7. washThe obtained solid was further washed with 5% ethyl acetate in pet. ether

출처 및 근거

ORD 기록
ord-7d996e1beb514a69997655bcafd7b903
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040562B2

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