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4-Nitrobenzyl bromide → 2-(p-Nitrobenzyl)-5-carbomethoxy-11-methyl-6H-pyrido [4,3-b] carbazolium Bromide

HRID 232179
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HRID 232179 반응식
[C:1]([CH2:5][C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:15]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)=[CH2:16])=[CH:12][CH:11]=[CH:10][CH:9]=2)([O:3][CH3:4])=[O:2].[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30][Br:31])=[CH:28][CH:27]=1)([O-:25])=[O:24].[Na].C(OCC)(=O)C1C=CC=NC=1.[K+].[Br-]>CO.CC(C)=O>[Br-:31].[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30][N+:19]2[CH:20]=[CH:21][C:22]3=[C:5]([C:1]([O:3][CH3:4])=[O:2])[C:6]4[NH:7][C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=5[C:14]=4[C:15]([CH3:16])=[C:17]3[CH:18]=2)=[CH:28][CH:27]=1)([O-:25])=[O:24]
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참가 물질

8

반응물 5

HCID 660114-Nitrobenzyl bromideHCID 69188Ethyl NicotinateHCID 253877Potassium BromideHCID 5360545SodiumHCID 13808959methyl 2-[3-(1-pyridin-3-ylethenyl)-1H-indol-2-yl]acetate

생성물 1

HCID 138089602-(p-Nitrobenzyl)-5-carbomethoxy-11-methyl-6H-pyrido [4,3-b] carbazolium Bromide

시약·촉매·용매 2

HCID 180Acetone용매HCID 887Methanol용매

실험 절차

Three grams (0.01 mol) of the ester 16 and 12.0 g (0.05 mol) of p-nitrobenzyl bromide in 140 mL of reagent grade acetone was stirred for 24 h. The crystals of 19 were collected, washed with ether, and dried; wt 4.72 g (92%). To a solution of 150 mg of metallic sodium in 40 mL of dry MeOH there were added 2.67 g (5.25 mmol) of crude 19 and 4.52 g (18.4 mmol) of ethyl nicotinate methobromide. The solution was stirred for 22 hours at room temperature in a nitrogen atmosphere. The crystallize solid that separated was filtered, washed with methanol, and dried; wt 2.31 g (80%) of the desired p-nitrobenzyl quaternary salt 22. The analytical sample was obtained by crystallization from CH2Cl2 -MeOH (1:1): mp 284°-289° C. dec; NMR (Me2SO-d6) δ12.13 (s, 1 H), 10.40 (s, 1 H), 9.31 (d, 1 H), 8.69 (d, 1 H), 8.49 (d, 1 H), 8.33 (d, 2 H), 7.86 (m, 3 H), 7.7-7.65 (m, 1 H), 7.50-7.47 (m, 1 H), 6.20 (s, 2 H), 4.13 (s, 3 H), 3.41 (s, 3 H); IR (KBr) 3240, 3045, 2945, 1717, 1590, 1420 cm-1.

후처리

  1. customThe crystals of 19 were collected
  2. washwashed with ether
  3. customdried
  4. customThe crystallize solid that separated
  5. filtrationwas filtered
  6. washwashed with methanol
  7. customdried
  8. customThe analytical sample was obtained by crystallization from CH2Cl2 -MeOH (1:1)

출처 및 근거

ORD 기록
ord-baf4e83b12394fc18036c410bd71d2e8
출처 데이터셋
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04851417

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