Water → HCID 131723089, compound

HRID 1250260Notes

Reaction equation

HRID 1250260 reaction equation
[O:1]=[C:2]([OH:14])[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].O.[CH3:16][NH:17][CH:18]([CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=1)[CH3:19]>CO>[O:1]=[C:2]([OH:14])[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH3:16][NH:17][CH:18]([CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=1)[CH3:19].[CH3:16][NH:17][CH:18]([CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=1)[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9794668HCID 9794668, compound

Product 1

HCID 131723089HCID 131723089, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In succession, galactaric acid (91 mg, 0.43 mmol) and water (0.4 mL) were added to a solution of (4E)-N-methyl-5-(4-methyl-3-nitrophenyl)-4-penten-2-amine (204 mg, 0.871 mmol) in methanol (4 mL). The mixture was warmed to 50° C. and filtered through a glass wool plug. The filtrate was diluted with ethanol (4 mL) and kept at −4° C. for 16 h. Filtration and vacuum drying at 40° C., gave 199 mg (68.2% yield) of yellow powder, mp 150-153° C.

Workup

  1. filtrationfiltered through a glass wool plug
  2. additionThe filtrate was diluted with ethanol (4 mL)
  3. filtrationFiltration and vacuum
  4. customdrying at 40° C.

Sources & evidence

ORD record
ord-c4031a7d93c741de82492ba891858a9e
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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