Toluene → HCID 17929730、化合物

HRID 1050692

反応式

HRID 1050692 の反応式
[CH:1]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=[O:15])[C:7]3=[C:8]2[C:3](=[C:4]([Br:16])[CH:5]=[CH:6]3)[CH:2]=1)=O.[CH2:17]([NH2:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>C(O)(=O)C>[Br:16][C:4]1[CH:5]=[CH:6][C:7]2[C:14](=[O:15])[N:23]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:11](=[O:13])[C:9]3[C:8]=2[C:3]=1[CH:2]=[CH:1][CH:10]=3

参加物

6

反応物 4

HCID 1140TolueneHCID 6212ChloroformHCID 8102HexylamineHCID 664931H,3H-Naphtho(1,8-cd)pyran-1,3-dione, 6-bromo-

生成物 1

HCID 17929730HCID 17929730、化合物収率 74.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 4-bromo-1,8-naphthalic anhydride (21.40 g, 77.2 mmol), n-hexylamine (13.1 mL, 100 mmol), toluene (200 mL), and chloroform (200 mL) was heated to boil for 1 hour. Precipitate formed making stirring difficult. The mixture was acidified with acetic acid, and heating was continued at 90° C. with distillation of chloroform. After all precipitate dissolved, the reaction mixture was poured onto crushed ice (300 g) and acidified with concentrated HCl to pH 1. After the ice melted, the solid was filtered off and dried. The crude product was purified by column chromatography (silica gel, hexane/ethyl acetate 2:1) to give 6-bromo-2-hexyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (20.66 g, 74%).

後処理

  1. temperaturewas heated
  2. customPrecipitate formed
  3. temperatureheating
  4. distillationwas continued at 90° C. with distillation of chloroform
  5. dissolutionAfter all precipitate dissolved
  6. additionthe reaction mixture was poured
  7. customonto crushed ice (300 g)
  8. filtrationthe solid was filtered off
  9. customdried
  10. customThe crude product was purified by column chromatography (silica gel, hexane/ethyl acetate 2:1)

出典と根拠

ORDレコード
ord-cb714efa8ddb440cbca5d203951d57bd
出典データセット
uspto-grants-2016_07
特許番号
US09382424B2

関連ノート

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