Tetrahydrothiopyran-4-one → 10-amino-3,4-dihydro-7-methyl-1H-thiopyrano[4,3-b]quinoline

HRID 274230

Reaction equation

HRID 274230 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5](=[CH:8][CH:9]=1)[C:6]#[N:7].[S:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1>[N+](C1C=CC=CC=1)([O-])=O>[NH2:7][C:6]1[C:5]2[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][C:4]=2[N:10]=[C:14]2[CH2:15][CH2:16][S:11][CH2:12][C:13]=12

Participants

4

Reactant 2

HCID 66173Tetrahydrothiopyran-4-oneHCID 28012762-Amino-4-methylbenzonitrile

Product 1

HCID 1458024610-amino-3,4-dihydro-7-methyl-1H-thiopyrano[4,3-b]quinolineYield 61.2%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-methylanthranilonitrile (4.46 g) and freshly fused zinc chloride (6.8 g) in 20 ml of nitrobenzene was heated at 50° C. for 1 hour. To this was added tetrahydrothiopyran-4-one (5.1 g) and the mixture was heated to 130° C. for 1.5 hours. After cooling, the zinc complex was filtered, rinsed with ethyl ether and partitioned between 2-butanone (MEK) and NH4OH. The aqueous phase was extracted with MEK and the organics were washed with water and dried (saturated NaCl, MgSO4). This was concentrated to give 4.76 g of an off-white powder, m.p. 239°-245° C. d., which was recrystallized from ethyl acetate to give 2.95 g of an off-white powder, m.p. 243°-246° C. d.

Workup

  1. temperaturethe mixture was heated to 130° C. for 1.5 hours
  2. temperatureAfter cooling
  3. filtrationthe zinc complex was filtered
  4. washrinsed with ethyl ether
  5. custompartitioned between 2-butanone (MEK) and NH4OH
  6. extractionThe aqueous phase was extracted with MEK
  7. washthe organics were washed with water
  8. dry with materialdried (saturated NaCl, MgSO4)
  9. concentrationThis was concentrated

Sources & evidence

ORD record
ord-6cbfcb18fdcd4d28be9155cdfde98cdc
Source dataset
uspto-grants-1995_02
Patent number
US05389629

Linked notes

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