N-methyl-2-pyrrolidone → HCID 86701360, compound

HRID 2179864Notes

Reaction equation

HRID 2179864 reaction equation
C([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:15]3[C:20]([CH:21]=[C:22]4[C:27]=2[CH:26]=[CH:25][CH:24]=[CH:23]4)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:6][CH:5]=1)C.Cl.N1C=CC=CC=1.CN1CCCC1=O>O>[CH:16]1[C:15]2[C:20](=[CH:21][C:22]3[C:27]([C:14]=2[C:7]2[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:4]([OH:3])=[CH:5][CH:6]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 10176127Pyridinium chlorideHCID 86701359HCID 86701359, compound

Product 1

HCID 86701360HCID 86701360, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

Under the nitrogen atmosphere, 9-(4-ethoxynaphthalen-1-yl)anthracene (87.1 g) as the fourteenth intermediate compound, pyridine hydrochloride (289.0 g) and 1-methyl-2-pyrrolidone (87 ml) were added to a flask, and stirred for 16 hours at 175° C. The reaction solution was cooled to room temperature, added with water, and washed while being heated. After suction filtration, the solid remained after dissolution was collected. The obtained solid was washed with methanol while being heated. It was then dissolved in heated chlorobenzene and subjected to suction filtration by using a Kiriyama funnel layered with silica gel. An appropriate amount of filtrate was distilled off under reduced pressure, and by adding heptane, re-precipitation was performed to give 4-(anthracen-9-yl)naphthalen-1-ol (74.3 g) as a fifteenth intermediate compound. The scheme is shown in the following “Reaction 26”.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washwashed
  3. temperaturewhile being heated
  4. filtrationAfter suction filtration
  5. dissolutionafter dissolution
  6. customwas collected
  7. washThe obtained solid was washed with methanol
  8. temperaturewhile being heated
  9. dissolutionIt was then dissolved in heated chlorobenzene
  10. filtrationsubjected to suction filtration
  11. distillationAn appropriate amount of filtrate was distilled off under reduced pressure
  12. additionby adding
  13. customheptane, re-precipitation

Sources & evidence

ORD record
ord-553f0e7bf34341dbb3b5a0e5e0fdda11
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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