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Ethanol → 3-(2-Hydroxyimino-5-methylhexyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone

HRID 1087782
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HRID 1087782 반응식
Cl.[NH2:2][OH:3].[CH3:4][O:5][C:6]1[N:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([N:16]3[CH:24]([CH2:25][C:26](=O)[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:33])=[N:13]2)=[CH:8][CH:7]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:3][N:2]=[C:26]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:25][CH:24]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:33])[N:16]1[C:12]1[CH:11]=[CH:10][C:9]2[C:14](=[N:15][C:6]([O:5][CH3:4])=[CH:7][CH:8]=2)[N:13]=1
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참가 물질

6

반응물 4

HCID 702Ethanol2회HCID 10340Sodium Carbonate2회HCID 443297Hydroxyamine hydrochloride2회HCID 141821822-(7-Methoxy-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-1-isoindolinone

생성물 1

HCID 867442493-(2-Hydroxyimino-5-methylhexyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone수율 22.4%

시약·촉매·용매

1
HCID 962Water용매3회

실험 절차

Hydroxylamine hydrochloride (0.9 g) is added to a suspension, maintained at 0° C. with a bath of ice-cold water, of 2-(7-methoxy-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-1-isoindolinone (4.3 g) in a mixture (100 cc) of water and ethanol (50:50 by volume). The suspension obtained is allowed to return to a temperature in the region of 20° C. and a solution of sodium carbonate (0.7 g) in distilled water (10 cc) is added. The suspension obtained is heated to reflux for 22 hours. During this period, ethanol (80 cc) is added in two portions. Refluxing is maintained for 12 hours, adding in three portions further hydroxylamine hydrochloride (1.35 g) and sodium carbonate (1.05 g). The reaction mixture is then poured into water (1 litre). The aqueous phase is extracted with methylene chloride (3×300 cc). The organic phases are combined, washed with distilled water (2×100 cc), dried over magnesium sulphate, filtered and concentrated to dryness. After recrystallization in 2-propanol, 3-(2-hydroxyimino-5-methylhexyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (1 g), m.p. 200° C., is obtained.

후처리

  1. customThe suspension obtained
  2. customto return to a temperature in the region of 20° C.
  3. customThe suspension obtained
  4. temperatureis heated
  5. temperatureto reflux for 22 hours
  6. waitDuring this period
  7. temperatureRefluxing
  8. temperatureis maintained for 12 hours
  9. extractionThe aqueous phase is extracted with methylene chloride (3×300 cc)
  10. washwashed with distilled water (2×100 cc)
  11. dry with materialdried over magnesium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness
  14. customAfter recrystallization in 2-propanol

출처 및 근거

ORD 기록
ord-5b04dde0fcac4252a04cbbbf8a68e6db
출처 데이터셋
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04960779

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