p-Toluenesulfonic acid → 8-fluoro-1,4,5,6-tetrahydrobenzo[h]quinolin-3(2H)-one

HRID 569646Notes

Reaction equation

HRID 569646 reaction equation
[F:1][C:2]1C=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=[O:12])[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:14]=[CH:15][C:16]2[C:17]3[NH:13][CH2:8][C:7](=[O:12])[CH2:6][C:5]=3[CH2:4][CH2:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

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

Product 1

HCID 221654778-fluoro-1,4,5,6-tetrahydrobenzo[h]quinolin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

16.7 g of 6-fluoro-3,4-dihydro-2(1H)-naphthalenone were boiled at reflux for 2.5 hours in 200 ml of benzene and 8.4 ml of pyrrolidine in the presence of 0.35 g of anhydrous p-toluenesulphonic acid. The crude 1-(6-fluoro-3,4-dihydro-2-naphthyl)pyrrolidine obtained was, without further purification, treated with 10.8 g of acrylamide and 0.5 g of p-toluenesulphonic acid. The mixture was heated under nitrogen to 100° for 2 hours and to 150° for 2 hours. The reaction mixture was dissolved in 180 ml of chloroform and washed with water. The organic phase was filtered over 150 g of silica gel (particle size 0.2-0.5 mm) while eluting with chloroform. After recrystallization from ethyl acetate there was obtained 8-fluoro-1,4,5,6-tetrahydrobenzo[h]quinolin-3(2H)-one of melting point 223°-224°.

Workup

  1. customThe crude 1-(6-fluoro-3,4-dihydro-2-naphthyl)pyrrolidine obtained
  2. customwas, without further purification
  3. additiontreated with 10.8 g of acrylamide and 0.5 g of p-toluenesulphonic acid
  4. temperatureThe mixture was heated under nitrogen to 100° for 2 hours and to 150° for 2 hours
  5. dissolutionThe reaction mixture was dissolved in 180 ml of chloroform
  6. washwashed with water
  7. filtrationThe organic phase was filtered over 150 g of silica gel (particle size 0.2-0.5 mm)
  8. washwhile eluting with chloroform
  9. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6be4f15b904343498aa0c32422aa59cf
Source dataset
uspto-grants-1988_03
Patent number
US04732979

Reaction notes

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