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Sodium Hydroxide → 1-(2-Methoxyphenyl)-4-amino-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline

HRID 729084
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HRID 729084 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH3:23])[C:15]=3[NH:14][C:13](=O)[C:12]=2[CH2:11][CH2:10]1.P(N)([NH2:34])(=O)OC1C=CC=CC=1.[OH-].[Na+]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH3:23])[C:15]=3[N:14]=[C:13]([NH2:34])[C:12]=2[CH2:11][CH2:10]1
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5

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HCID 14798Sodium HydroxideHCID 81954Phenyl phosphorodiamidate2회HCID 157498161-(2-Methoxyphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline

생성물 1

HCID 157498211-(2-Methoxyphenyl)-4-amino-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline수율 24.1%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매

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온도
230 °C

실험 절차

1-(2-Methoxyphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline (1.5 g) and phenyl phosphorodiamidate (2.5 g) were fused at 230° C. After 45 minutes the mixture was diluted with diphenyl ether (10 ml), further phenyl phosphorodiamidate (2 g) added, and heated for a further 15minutes at 230° C. Aqueous sodium hydroxide was added and the product extracted into dichloromethane. Chromatography (silica gel. 2.5-4%methanolic ammonia in dichloromethane) to remove unchanged starting material was followed by recrystallisation from ethanol/ethyl acetate to yield 1-(2-methoxyphenyl)-4-amino-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline (0.36 g), m.p. 244°-247° (dec).

후처리

  1. customwere fused at 230° C
  2. additionadded
  3. extractionthe product extracted into dichloromethane
  4. customChromatography (silica gel. 2.5-4%methanolic ammonia in dichloromethane) to remove unchanged
  5. customwas followed by recrystallisation from ethanol/ethyl acetate

출처 및 근거

ORD 기록
ord-cdad40774a3b4704af12b9b0a2d3f3f8
출처 데이터셋
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05051508

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