N-methyl-2-pyrrolidone → HCID 68184795, compound

HRID 2179853Notes

Reaction equation

HRID 2179853 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=3)=[CH:10]2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1.CN1CCCC1=O>O>[CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([OH:2])[CH:12]=2)[CH:7]=[CH:8][C:9]=1[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 10176127Pyridinium chlorideHCID 12350939HCID 12350939, compound

Product 1

HCID 68184795HCID 68184795, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

Under the nitrogen atmosphere, 7-methoxy-2,2′-binaphthalen (31.0) as the sixth intermediate compound, pyridine hydrochloride (63.0 g) and N-methylpyrrolidone (20 ml) were added to a flask and then stirred for 7 hours at 200° C. Once the heating is completed, it was cooled to 100° C. or less and added with water. The solid precipitated by adding water was collected by suction filtration. The obtained solid was purified by silica gel column chromatography (solvent: toluene) to give [2,2′-binaphthalen]-7-ol (22.0 g) as a seventh intermediate compound. The scheme is shown in the following “Reaction 12”.

Workup

  1. temperatureit was cooled to 100° C. or less
  2. customThe solid precipitated
  3. additionby adding water
  4. filtrationwas collected by suction filtration
  5. customThe obtained solid was purified by silica gel column chromatography (solvent: toluene)

Sources & evidence

ORD record
ord-5c7c1978d4e6482dbe0bba6c84ed27ce
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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