Acetone → 8-((4-Isopropylamino-1-methylbutyl)amino)-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline Succinate

HRID 1388571Notes

Reaction equation

HRID 1388571 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]([NH:7][C:8]1[CH:9]=[C:10]([O:30][CH3:31])[C:11]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[C:13]2[CH3:18])[CH3:6].[CH3:32][C:33]([CH3:35])=O.[C:36]([OH:43])(=[O:42])[CH2:37][CH2:38][C:39]([OH:41])=[O:40]>CCO.[Pt]=O>[C:36]([OH:43])(=[O:42])[CH2:37][CH2:38][C:39]([OH:41])=[O:40].[CH:33]([NH:1][CH2:2][CH2:3][CH2:4][CH:5]([NH:7][C:8]1[CH:9]=[C:10]([O:30][CH3:31])[C:11]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=2)=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[C:13]2[CH3:18])[CH3:6])([CH3:35])[CH3:32]

Participants

6

Reactant 3

HCID 180Acetone2×HCID 1110Succinic AcidHCID 456317WR 225448

Product 1

HCID 204712578-((4-Isopropylamino-1-methylbutyl)amino)-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline Succinate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 8-(4-amino-1-methylbutylamino)-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline as the free base (4.7 g, 10.8 mmol) prepared as in Example 1 in EtOH (60 mL) containing acetone (1.8 mL), prereduced platinum oxide (0.6 g) and molecular sieves (3A) was reduced on a Parr apparatus at 45 psig for 5 hours. An additional quantity of acetone (0.9 mL) was added and the reduction was continued an additional 18 hours. The catalyst and molecular sieves were filtered (celite) and the solvent was removed in vacuo. The residue was dissolved in acetonitrile (50 mL) and succinic acid (1.35 g, 1 mol equivalent) was added with stirring. The solid was filtered after cooling in the refrigerator overnight to yield the title compound 5, 5.8 g (91%), mp 143°-146°. Recrystallization from acetonitrile (75 mL) yielded pure title compound, 5.2 g, (81%), mp 145°-147.5°.

Workup

  1. waitthe reduction was continued an additional 18 hours
  2. filtrationThe catalyst and molecular sieves were filtered (celite)
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in acetonitrile (50 mL)
  5. filtrationThe solid was filtered
  6. temperatureafter cooling in the refrigerator overnight

Sources & evidence

ORD record
ord-041e7483417445319b39d5df2d0eed6b
Source dataset
uspto-grants-1984_02
Patent number
US04431807

Reaction notes

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