Triethylamine → HCID 20393417, compound

HRID 1863116Notes

Reaction equation

HRID 1863116 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:16][CH3:17])[C:5]([O:14][CH3:15])=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[C:7]2[CH3:13].I[CH2:19][CH2:20][CH2:21][CH:22]([N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])[CH3:23].C(N(CC)CC)C>C(OCCO)C.C(=O)(O)[O-].[Na+]>[CH3:15][O:14][C:5]1[C:4]([O:16][CH3:17])=[CH:3][C:2]([NH:1][CH2:19][CH2:20][CH2:21][CH:22]([N:24]2[C:25](=[O:34])[C:26]3=[CH:33][CH:32]=[CH:31][CH:30]=[C:27]3[C:28]2=[O:29])[CH3:23])=[C:11]2[C:6]=1[C:7]([CH3:13])=[CH:8][C:9]([CH3:12])=[N:10]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6000781H-Isoindole-1,3(2H)-dione, 2-(4-iodo-1-methylbutyl)-HCID 612479HCID 612479, compound

Product 1

HCID 20393417HCID 20393417, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 8076Glycol monoethyl etherSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
135 °C

Procedure

A solution of 8-amino-5,6-dimethoxy-2,4-dimethylquinoline (20.0 g, 86 mmole), 1-iodo-4-phthalimidopentane (38.4 g, 112 mmole) and triethylamine (11.3 g, 112 mmole) in 2-ethoxyethanol (230 ml) was heated at reflux (135° C.) for 5 hr. After cooling, the solution was diluted with 5% aqueous sodium bicarbonate (0.5 l) and then extracted with methylene chloride (2× 250 ml). The combined extracts were washed with water (2× 250 ml) and brine (100 ml) and then dried (potassium carbonate). Filtration, then evaporation of the solvents, afforded a black tar. The tar was chromatographed over silica gel (0.7 kg) with benzene. The orange-brown material eluting first from the column was crystallized from ethanol (10% solution), affording 12.7 g (33%) of the title compound as orange plates, mp 141°-144°. Further recrystallization of a small amount gave an analytical sample with mp 144.5°-146.5°; the analysis was satisfactory after drying at 110° (the analysis corresponded to a hemihydrate after drying at 78°).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride (2× 250 ml)
  3. washThe combined extracts were washed with water (2× 250 ml) and brine (100 ml)
  4. dry with materialdried (potassium carbonate)
  5. filtrationFiltration
  6. customevaporation of the solvents
  7. customafforded a black tar
  8. customThe tar was chromatographed over silica gel (0.7 kg) with benzene
  9. washThe orange-brown material eluting first from the column
  10. customwas crystallized from ethanol (10% solution)

Sources & evidence

ORD record
ord-024359a7135c4adf902f21455a389f17
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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