Hydrogen Bromide → 5-[p-Chlorophenoxy]-6-methoxy-8-[4-phthalimido-1-methylbutylamino]quinoline

HRID 1863109Notes

Reaction equation

HRID 1863109 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:20][CH3:21])[C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Br[CH:23]([CH3:38])[CH2:24][CH2:25][CH2:26][N:27]1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37].C(N(CC)CC)C.Br>CC(C)=O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:5]2[C:4]([O:20][CH3:21])=[CH:3][C:2]([NH:1][CH:23]([CH3:38])[CH2:24][CH2:25][CH2:26][N:27]3[C:31](=[O:32])[C:30]4=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]4[C:28]3=[O:37])=[C:11]3[C:6]=2[CH:7]=[CH:8][CH:9]=[N:10]3)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 240534N-(4-Bromopentyl)phthalimideHCID 6052298-Amino-5-[p-chlorophenoxy]-6-methoxy quinoline

Product 1

HCID 6299635-[p-Chlorophenoxy]-6-methoxy-8-[4-phthalimido-1-methylbutylamino]quinolineYield 79.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 8-amino-5-(4-chlorophenoxy)- 6-methoxyquinoline (6.2 g, 0.02 mole), 4-bromo-1-phthalimidopentane (6.0 g, 0.02 mole), and triethylamine (2.0 g, 0.02 mole) was heated at 130°-135° for 12 hr. The cooled mixture was extractively treated with arm acetone (50 ml), cooled, and triethylamine hydrobromide collected (3.2 g, 89%). The filtrates were concentrated to dryness, and the residues taken up in chloroform, then treated with 48% hydrobromic acid. The chloroform layer was dried and concentrated, then absolute ether added to precipitate the hydrobromide of the desired compound (8.2 g, 70% yield). As obtained, the hydrobromide melted 194°-198°; following crystallization from ethanol, mp 214°-215°. It analyzed as a monohydrate. The base was liberated as a crystalline solid of mp 75°-77°.

Workup

  1. temperaturewas heated at 130°-135° for 12 hr
  2. temperaturecooled
  3. customtriethylamine hydrobromide collected (3.2 g, 89%)
  4. concentrationThe filtrates were concentrated to dryness
  5. additiontreated with 48% hydrobromic acid
  6. dry with materialThe chloroform layer was dried
  7. concentrationconcentrated
  8. additionabsolute ether added

Sources & evidence

ORD record
ord-6a25f58391dd426b8e92289aa853edce
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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