Isobutylamine → HCID 178449195, compound

HRID 374829Notes

Reaction equation

HRID 374829 reaction equation
C(N=C1C=CC=CC1O[CH:13]=[N:14][C:15]1[CH:16]=[C:17](/[C:21](/[C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:22]\[CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])[CH:18]=[CH:19][CH:20]=1)(=O)C1C=CC=CC=1.[CH3:40][CH:41]([CH3:44])[CH2:42][NH2:43].[OH-:45].[Na+]>C(O)(C)C>[C:42]([N:43]=[C:13]([NH:32][CH2:31][CH:30]([CH3:35])[CH3:21])[NH:14][C:15]1[CH:16]=[C:17](/[C:21](/[C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:22]\[CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:18]=[CH:19][CH:20]=1)(=[O:45])[C:41]1[CH:44]=[CH:16][CH:15]=[CH:20][CH:40]=1

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 14798Sodium HydroxideHCID 86749197HCID 86749197, compound

Product 1

HCID 178449195HCID 178449195, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

2.6 g methyl 5E-6-(3-(benzoylimino-phenoxymethyleneamino)phenyl)-6-(3-pyridyl)hex-5-enoate and 5 ml of 2-methylpropylamine are refluxed for 1 hour in 50 ml of isopropanol. The reaction mixture is cooled to 50° C., mixed with 15 ml of 1N sodium hydroxide solution and stirred for 30 minutes at this temperature. The solvent is removed, the residue is taken up in water and washed with ethyl acetate. The aqueous phase is adjusted to a pH value of 4-5 by the addition of citric acid, the precipitate formed is suction filtered and washed with water. The filter cake is recrystallised from ethyl acetate.

Workup

  1. customThe solvent is removed
  2. washwashed with ethyl acetate
  3. additionThe aqueous phase is adjusted to a pH value of 4-5 by the addition of citric acid
  4. customthe precipitate formed
  5. filtrationfiltered
  6. washwashed with water
  7. customThe filter cake is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-3787ff87e4254678b5788c7d1a3b509f
Source dataset
uspto-grants-1996_01
Patent number
US05482948

Reaction notes

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