Chloroform → methyl 11-methyl-6H-pyrido[4,3-b]carbazole-5-carboxylate

HRID 232180노트

반응식

HRID 232180 반응식
[Na].[Br-].[N+](C1C=CC(C[N+:11]2[CH:32]=[CH:31][C:14]3=[C:15]([C:27]([O:29][CH3:30])=[O:28])[C:16]4[NH:17][C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=5[C:24]=4[C:25]([CH3:26])=[C:13]3[CH:12]=2)=CC=1)([O-])=O.N(C1C=CC(N(C)C)=CC=1)=O.C(Cl)(Cl)Cl>CO>[C:27]([C:15]1[C:16]2[NH:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[C:24]=2[C:25]([CH3:26])=[C:13]2[CH:12]=[N:11][CH:32]=[CH:31][C:14]=12)([O:29][CH3:30])=[O:28]

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 8749N,N-dimethyl-4-nitrosoanilineHCID 5360545SodiumHCID 138089602-(p-Nitrobenzyl)-5-carbomethoxy-11-methyl-6H-pyrido [4,3-b] carbazolium Bromide

생성물 1

HCID 13808962methyl 11-methyl-6H-pyrido[4,3-b]carbazole-5-carboxylate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 200 mg (13 mmol) of metallic sodium in 600 mL of dry MeOH there were added 2.70 g (5.3 mmol) of the quaternary salt 22, 1.06 g (6.3 mmol) of p-nitrosodimethylaniline, and 300 mL of dry CHCl3. The suspension was stirred overnight at room temperature in a nitrogen atmosphere and then evaporated to dryness. The residue was suspended in a solution of 30 mL of CHCl3 and 5 mL of MeOH and flash chromatographed on a column of 40 g of silica gel with ether-triethylamine (20:1) as the eluant. The purest fraction was set aside and the less pure material was rechromatographed. The process was repeated, and the purest fractions which showed essentially only one spot on TLC were combined; wt 715 mg (47%). After crystallization from EtOAc-CH2Cl2 (5:1), the yellow needles melted at 203°-204° C. dec: NMR (Me2SO-d6) 11.56 (s, 1 H), 9.73 (s, 1 H), 8.87 (d, 1 H), 8.53 (d, 1 H), 8.38 (d, 1 H), 7.80 (d, 1 H), 7.60-7.52 (m, 1 H), 7.30-7.29 (m, 1 H), 4.10 (s, 3 H), 3.33 (s, 3 H); IR (KBr) 3300, 2950, 1675, 1600, 1465 cm-1.

후처리

  1. customevaporated to dryness
  2. customchromatographed on a column of 40 g of silica gel with ether-triethylamine (20:1) as the eluant
  3. customthe less pure material was rechromatographed
  4. customAfter crystallization from EtOAc-CH2Cl2 (5:1)

출처 및 근거

ORD 기록
ord-71b580decefb431da1e670d2bb082059
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851417

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