2H-thiopyran-2-one → 10-amino-3,4-dihydro-7-fluoro-1H-thiopyrano [4,3-b]quinoline

HRID 359699Notes

Reaction equation

HRID 359699 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5](=[CH:8][CH:9]=1)[C:6]#[N:7].[S:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=O>[N+](C1C=CC=CC=1)([O-])=O.[Cl-].[Cl-].[Zn+2]>[NH2:7][C:6]1[C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][C:4]=2[N:10]=[C:14]2[CH2:15][CH2:16][S:11][CH2:12][C:13]=12

Participants

5

Reactant 2

HCID 6380022H-thiopyran-2-oneHCID 99421582-Amino-4-fluorobenzonitrile

Product 1

HCID 1458024710-amino-3,4-dihydro-7-fluoro-1H-thiopyrano [4,3-b]quinolineYield 62.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7416NitrobenzeneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-fluoroanthranilonitrile (4.47 g) and freshly fused, pulverized ZnCl2 (6.7 g) in 20 ml of nitrobenzene was heated at 50° C. for 45 minutes. To the resulting suspension was added thiopyran-2-one (5.1 g). This was heated at 130° C. for 3 hours. The resulting precipitate was filtered, rinsed with ether and partioned between 2-butanone and NH4OH solution. The aqueous layer was extracted with 2-butanone and the combined organics were washed with water and dried (MgSO4). The resulted in 4.8 g of a tan solid, m.p. 234°-237° C. d., which was recrystallized from ethyl acetate to give 3.0 g of a white powder, m.p. 235°-237° C. d.

Workup

  1. temperatureThis was heated at 130° C. for 3 hours
  2. filtrationThe resulting precipitate was filtered
  3. washrinsed with ether
  4. extractionThe aqueous layer was extracted with 2-butanone
  5. washthe combined organics were washed with water
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-01a1e548f4834cd9b14e23253aaa1b22
Source dataset
uspto-grants-1991_03
Patent number
US05002955

Reaction notes

Loading…