Chloroform → 5,6-Dimethoxy-4-methyl-8-(4-phthalimido-1-ethylbutylamino)quinoline hydrochloride

HRID 1863114Notes

Reaction equation

HRID 1863114 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([NH2:16])[CH:8]=[C:9]([O:14][CH3:15])[C:10]=2[O:12][CH3:13])[N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24]1(=[O:41])[N:28]([CH2:29][CH2:30][CH2:31][CH:32](I)[CH2:33][CH3:34])[C:27](=[O:36])[C:26]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:25]12.C(Cl)(Cl)[Cl:43]>C(OCCO)C>[ClH:43].[CH3:13][O:12][C:10]1[C:9]([O:14][CH3:15])=[CH:8][C:7]([NH:16][CH:32]([CH2:33][CH3:34])[CH2:31][CH2:30][CH2:29][N:28]2[C:24](=[O:41])[C:25]3=[CH:40][CH:39]=[CH:38][CH:37]=[C:26]3[C:27]2=[O:36])=[C:6]2[C:11]=1[C:2]([CH3:1])=[CH:3][CH:4]=[N:5]2

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471Triethylamine2×HCID 6090098-Amino-5,6-dimethoxy-4-methylquinolineHCID 127813511-Phthalimido-4-iodohexane

Product 1

HCID 127813565,6-Dimethoxy-4-methyl-8-(4-phthalimido-1-ethylbutylamino)quinoline hydrochlorideYield 63%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 4-methyl-5,6-dimethoxy-8-aminoquinoline (0.042 mole) in 2-ethoxyethanol (21 ml) containing triethylamine (5.8 ml) and 1-phthalimido-4-iodohexane (14.9 g, 0.042 mole) was heated at 110° for 2.5 hr. Thereafter, there were two incremental additions of triethylamine and side-chain over 6 hrs, and the heating at 110° continued overnight. Th reaction mixture was diluted with chloroform and washed with water (×2). The organic layer was dried (K2CO3) and the solvents were removed in vacuo. The residue was dissolved in ether, filtered and acidified with excess ethereal HCl. The red gum which separated was crystallized from ethanol (150 ml) to yield 5,6-dimethoxy-4-methyl-8-(4-phthalimido-1-ethylbutylamino)quinoline hydrochloride (13 g, 63%), mp 163°-166°.

Workup

  1. temperaturewas heated at 110° for 2.5 hr
  2. customover 6 hrs
  3. washwashed with water (×2)
  4. dry with materialThe organic layer was dried (K2CO3)
  5. customthe solvents were removed in vacuo
  6. dissolutionThe residue was dissolved in ether
  7. filtrationfiltered
  8. customThe red gum which separated
  9. customwas crystallized from ethanol (150 ml)

Sources & evidence

ORD record
ord-743d477c3b4b47aab0c900b4dfaf9178
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

Loading…