Water → HCID 131723091, compound

HRID 1250268Notes

Reaction equation

HRID 1250268 reaction equation
[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH2:15])[CH:9]=1)[CH3:4].[O:16]=[C:17]([OH:29])[C@@H:18]([C@H:20]([C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23])[OH:21])[OH:19].O>C(O)C>[O:16]=[C:17]([OH:29])[C@@H:18]([C@H:20]([C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23])[OH:21])[OH:19].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH2:15])[CH:9]=1)[CH3:4].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH2:15])[CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10198149HCID 10198149, compound

Product 1

HCID 131723091HCID 131723091, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a hot solution of (4E)-N-methyl-5-(3-amino-4-methylphenyl)-4-penten-2-amine (900 mg, 4.41 mmol) in ethanol (40 mL) was added galactaric acid (463 mg, 2.20 mmol). The mixture was heated to reflux and water (0.5 mL) was added drop-wise. The clear solution was filtered to remove some insoluble particles. The filtrate was concentrated to 25 mL and cooled to ambient temperature. The precipitate was filtered, washed with anhydrous ether and dried in a vacuum oven at 45° C. for ˜16 h. The yield was 1.16 g (85.6%) of a white powder, mp 186-189° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationThe clear solution was filtered
  4. customto remove some insoluble particles
  5. concentrationThe filtrate was concentrated to 25 mL
  6. filtrationThe precipitate was filtered
  7. washwashed with anhydrous ether
  8. customdried in a vacuum oven at 45° C. for ˜16 h

Sources & evidence

ORD record
ord-5adb44be4e8c4da5bb948919e50a2e54
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

Loading…