Iodoethane → 2-Methyl-4-ethylaminobenzaldehyde

HRID 565799노트

반응식

HRID 565799 반응식
[CH3:1][C:2]1[CH:9]=[C:8]([NH:10][C:11](=O)[CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(I)C.CC(C)([O-])C.[K+].[OH-].[Na+]>O>[CH3:1][C:2]1[CH:9]=[C:8]([NH:10][CH2:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

참가 물질

6

반응물 4

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 12931765N-(4-Formyl-3-methylphenyl)acetamideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 221120842-Methyl-4-ethylaminobenzaldehyde수율 58%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of purified 2-methyl-4-acetamidobenzaldehyde (9.6 g, 0.054 mole), ethyl iodide (10 ml, 0.125 mole), and 50 ml of tetrahydrofaran was warmed to about 300 with stirring under a nitrogen atmosphere. Solid potassium t-butoxide (6.25 g, 0.056 mole) was added and the mixture was stirred for 2.5 hr at 30°. The mixture was concentrated under vacuum at 50° on a rotary evaporator to a syrup. The syrup was dissolved in methanol (30 ml) before adding water (20 ml) and then sodium hydroxide (5 g, 0.125 mole) to the mixture. After heating the mixture to reflux temperature for 30 min, it was cooled to rt and water (120 ml) was added. Solid product precipitated on stirring over night. After filtering and drying, 5.1 g (58%) of 2-methyl-4-ethylaminobenzaldehyde was obtained.

후처리

  1. temperatureof tetrahydrofaran was warmed to about 300
  2. stirringthe mixture was stirred for 2.5 hr at 30°
  3. concentrationThe mixture was concentrated under vacuum at 50° on a rotary evaporator to a syrup
  4. dissolutionThe syrup was dissolved in methanol (30 ml)
  5. additionbefore adding water (20 ml)
  6. temperatureAfter heating the mixture
  7. temperatureto reflux temperature for 30 min
  8. customSolid product precipitated
  9. stirringon stirring over night
  10. filtrationAfter filtering
  11. customdrying

출처 및 근거

ORD 기록
ord-9fe1427852194cb29956f66beabdc7be
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172260B2

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