4-Nitrobenzyl bromide → HCID 13808960, Verbindung

HRID 232179

Reaktionsgleichung

Reaktionsgleichung von HRID 232179
[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]

Komponenten

8

Edukt 5

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

Produkt 1

HCID 13808960HCID 13808960, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-baf4e83b12394fc18036c410bd71d2e8
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851417

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