Methanol → 1,4-Pentanediamine, N(sup 4)-(6-methoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-, butanedioate (1:1)

HRID 1388568Notes

Reaction equation

HRID 1388568 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([NH:25][CH:26]([CH3:41])[CH2:27][CH2:28][CH2:29][N:30]3C(=O)C4=CC=CC=C4C3=O)[CH:8]=[C:9]([O:23][CH3:24])[C:10]=2[O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:5]=[CH:4][CH:3]=1.O.NN.[C:45]([OH:52])(=[O:51])[CH2:46][CH2:47][C:48]([OH:50])=[O:49].CO>C(O)C.CCOCC>[C:45]([OH:52])(=[O:51])[CH2:46][CH2:47][C:48]([OH:50])=[O:49].[NH2:30][CH2:29][CH2:28][CH2:27][CH:26]([NH:25][C:7]1[CH:8]=[C:9]([O:23][CH3:24])[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[CH3:1])[CH3:41]

Participants

7

Reactant 4

HCID 887MethanolHCID 1110Succinic Acid2×HCID 24654Hydrazine hydrate (1:1)HCID 130042054-Methyl-5-(3-trifluoromethylphenoxy)-6-methoxy-8-(4-phthalimido-1-methylbutylamino)quinoline

Product 1

HCID 30619681,4-Pentanediamine, N(sup 4)-(6-methoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-, butanedioate (1:1)Yield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of the phthalimide VIII (4.9 g, 8.7 mmol) in ethanol (110 mL) containing hydrazine hydrate (75%, 1.48 mL) was heated at reflux for 6 hours. The ethanol was removed under reduced pressure and the residue was shaken with ether and 10% aqueous potassium hydroxide. The ether layer was washed with water (×2) and dried (K2CO3). To the dried ether solution of 1 as the free base, was added a solution of succinic acid (1.03 g, 1 mol equiv) in ether (100 mL) containing methanol (4 mL) to solubilize the succinic acid. After standing overnight, the solid was filtered to yield 4.5 g (94%) of the target compound (1), mp 102°-103° (eff).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customThe ethanol was removed under reduced pressure
  4. washThe ether layer was washed with water (×2)
  5. dry with materialdried (K2CO3)
  6. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-17973dcb02434e2797d349e53f00f7b7
Source dataset
uspto-grants-1984_02
Patent number
US04431807

Reaction notes

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