4-Nitrobenzyl bromide → HCID 13808960、化合物

HRID 232179

反応式

HRID 232179 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

HCID 13808960HCID 13808960、化合物

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-baf4e83b12394fc18036c410bd71d2e8
出典データセット
uspto-grants-1989_07
特許番号
US04851417

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