1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 178479603, compound

HRID 745954Notes

Reaction equation

HRID 745954 reaction equation
CO[NH:3][C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:7]=[CH:6][C:5]=1[C:14](=[O:23])[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.C1(OC2C=CC=CC=2)C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1>>[ClH:22].[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([N:15]2[C:14](=[O:23])[C:5]3=[CH:6][NH:7][C:8]4[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=4[C:4]3=[N:3]2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 13787235HCID 13787235, compound

Product 1

HCID 178479603HCID 178479603, compound

Procedure

The mixture of 0.3 g of 4-(O-methylhydroxylamino)-3-(N-p-chlorophenylcarbamoyl)-5,6,7,8-tetrahydroquinoline and 15 mL of eutectic diphenyl ether-biphenyl is heated to 240° for 2 hours under nitrogen. It is cooled to room temperature, concentrated under high vacuum, and the residue is diluted with 100 mL of petroleum ether, and filtered. The collected solid is stirred with 15 mL of diethyl ether and 3 mL of 2N aqueous sodium hydroxide for 1 hour, filtered to remove insoluble material and the layers of filtrate are separated. The aqueous phase is treated with 0.3 g of ammonium chloride to give a yellow precipitate, which is collected and recrystallized from isopropanol containing hydrogen chloride to yield the 2-p-chlorophenyl-2,3,6,7,8,9-hexahydropyrazolo[4,3-c]quinolin-3(5H)-one hydrochloride.

Workup

  1. temperatureis heated to 240° for 2 hours under nitrogen
  2. concentrationconcentrated under high vacuum
  3. additionthe residue is diluted with 100 mL of petroleum ether
  4. filtrationfiltered
  5. filtrationfiltered
  6. customto remove insoluble material
  7. customthe layers of filtrate are separated
  8. additionThe aqueous phase is treated with 0.3 g of ammonium chloride
  9. customto give a yellow precipitate, which
  10. customis collected
  11. customrecrystallized from isopropanol
  12. additioncontaining hydrogen chloride

Sources & evidence

ORD record
ord-0ecd1ce33edb44e2bac4e2a14ae92698
Source dataset
uspto-grants-1986_07
Patent number
US04602014

Reaction notes

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