Diisopropylamine → HCID 12385317, compound

HRID 1863124Notes

Reaction equation

HRID 1863124 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12].Br[CH:16]([N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(NC(C)C)(C)C>C(O)C.C(OCCO)C.CCOCC>[CH3:14][O:13][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([NH:1][CH:20]([CH3:21])[CH2:19][CH2:18][CH2:17][CH2:16][N:22]3[C:23](=[O:32])[C:24]4=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]4[C:26]3=[O:27])[CH:3]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 6047536-Methoxy-4-methyl-8-quinolinamineHCID 70607958HCID 70607958, compound

Product 1

HCID 12385317HCID 12385317, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

8-Amino-6-methoxy-4-methylquinoline (5.5 g, 0.03 mole), the above bromophthalimidohexane (8.2 g, 0.26 mole) and diisopropylamine (2.55 g) were dissolved in a mixture ethanol (4.3 ml) and 2-ethoxyethanol (4.3 ml). This solution was heated in a sealed tube at 150° for 3.5 hr. After cooling, the reaction mixture was diluted with ether (400 ml). Diisopropylamine hydrobromide was removed by filtration and the filtrate was concentrated to dryness. The residue crystallized upon trituration with EtOH (50 ml) to give the title compound (5.2 g, 47%), contaminated with a trace amount of starting material. Additional starting 8-aminoquinoline could be recovered from the ethanol filtrate.

Workup

  1. temperatureThis solution was heated in a sealed tube at 150° for 3.5 hr
  2. temperatureAfter cooling
  3. customDiisopropylamine hydrobromide was removed by filtration
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe residue crystallized upon trituration with EtOH (50 ml)

Sources & evidence

ORD record
ord-acf43b9bb88447a5908699d992b7ad4c
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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