Toluene → HCID 17929730, compound

HRID 1050692

Reaction equation

HRID 1050692 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 17929730HCID 17929730, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-cb714efa8ddb440cbca5d203951d57bd
Source dataset
uspto-grants-2016_07
Patent number
US09382424B2

Linked notes

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