Nitrobenzene → HCID 21257364, compound

HRID 636074Notes

Reaction equation

HRID 636074 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4]([CH3:14])=[CH:5][C:6](=[O:13])[NH:7]2.[N+](C1C=CC=CC=1)([O-])=O.[Al+3].[Cl-].[Cl-].[Cl-].[C:28](Cl)(=[O:33])/[C:29](=[CH:31]/[CH3:32])/[CH3:30].C(N(CC)CC)C>C(Cl)(Cl)Cl.CO.C(=S)=S>[OH:1][C:2]1[CH:11]=[C:10]2[O:12][CH:31]([CH3:32])[CH:29]([CH3:30])[C:28](=[O:33])[C:9]2=[C:8]2[C:3]=1[C:4]([CH3:14])=[CH:5][C:6](=[O:13])[NH:7]2

Participants

9

Reactant 5

HCID 7416NitrobenzeneHCID 8471TriethylamineHCID 5325503(2E)-2-Methyl-2-butenoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21257365HCID 21257365, compound

Product 1

HCID 21257364HCID 21257364, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×HCID 6348Carbon DisulfideSolvent

Procedure

A mixture of compound 13 (11.2 g, 58.6 mmol), carbon disulfide (220 mL) and nitrobenzene (80 mL) in a RBF was treated with AlCl3 (38.93 g, 293 mmol) followed by tigloyl chloride (8.33 g, 70.3 mmol). After completion of reaction (TLC chloroform:methanol, 9:1, Rf=0.4) the reaction was worked up as described for preparation of compound 4 and further treatment with triethylamine (8.2 mL, 64.4 mmol) in chloroform (200 mL) as described for 4 gave a residue after work up. The residue on purification by column chromatography (silica gel, 60-120 mesh, chloroform : methanol, 19:1) furnished (±) 5-hydroxy4,8,9-trimethyl-1,8,9,10-tetrahydro-2H-pyrano[2,3-h]-quinoline-2,10-dione (15, 1.9 g) in 21% yield as a solid. M.P. 300° C.

Workup

  1. customgave a residue after work up
  2. customThe residue on purification by column chromatography (silica gel, 60-120 mesh, chloroform : methanol, 19:1)

Sources & evidence

ORD record
ord-683319daf4b6438cab5daaef06f2ff45
Source dataset
uspto-grants-2001_02
Patent number
US06191279B1

Reaction notes

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