p-Toluenesulfonic acid → HCID 10465943, compound

HRID 1639370Notes

Reaction equation

HRID 1639370 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 50443856-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 10465943HCID 10465943, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

16.7 g of 6-fluoro-3,4-dihydro-2(1H)-naphthalenone in 200 ml of benzene are boiled at reflux for 2.5 hours with 8.4 ml of pyrrolidine and 0.35 g of anhydrous p-toluenesulfonic acid. The 1-(6-fluoro-3,4-dihydro-2-naphthyl)pyrrolidine obtained is treated, without purification, with 10.8 g of acrylamide and 0.5 g of p-toluenesulfonic acid. The mixture is heated under nitrogen at 100° for 2 hours and at 150° for 2 hours. The mixture is dissolved in 180 ml of chloroform, washed with water and chromatographed over 150 g of silica gel with chloroform. Recrystallization from ethyl acetate gives 8-fluoro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one with melting point 223°-224°.

Sources & evidence

ORD record
ord-e3b1a8e00c1c47e483b5f64496b92707
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

Loading…