Water → 9-[(3-Hydroxy-5-methoxyphenyl)amino]-1,2-dihydrothieno[3,2-f]quinoline-8-carbonitrile 3,3-dioxide

HRID 1817210Notes

Reaction equation

HRID 1817210 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[S:14](=[O:16])(=[O:15])[CH2:13][CH2:12][C:10]3=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[OH:19][C:20]1[CH:21]=[C:22]([CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1)[NH2:23].O.[Cl-].[NH4+]>C(O)(C)C>[OH:19][C:20]1[CH:21]=[C:22]([NH:23][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]4[S:14](=[O:16])(=[O:15])[CH2:13][CH2:12][C:10]4=3)[N:5]=[CH:4][C:3]=2[C:17]#[N:18])[CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 119535163-Amino-5-methoxyphenolHCID 578821969-Chloro-1,2-dihydrothieno[3,2-f]quinoline-8-carbonitrile 3,3-dioxide

Product 1

HCID 236344889-[(3-Hydroxy-5-methoxyphenyl)amino]-1,2-dihydrothieno[3,2-f]quinoline-8-carbonitrile 3,3-dioxideYield 22.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

65 mg (0.23 mmol) of 9-chloro-1,2-dihydrothieno[3,2-f]quinoline-8-carbonitrile 3,3-dioxide are refluxed together with 39 mg (1.2 eq., 0.28 mmol) of 3-hydroxy-5-methoxyaniline in 2 ml of isopropanol for 2 hours. After the reaction is complete, the crude product is mixed with water and sat. ammonium chloride solution, extracted 3× with dichloromethane/methanol, washed 1× with sat. sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. Final purification of the compound took place by chromatography. 20 mg (22%) of the desired product were obtained.

Workup

  1. extractionextracted 3× with dichloromethane/methanol
  2. washwashed 1× with sat. sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customFinal purification of the compound

Sources & evidence

ORD record
ord-c17f345a2bcc4097985d830c01c79681
Source dataset
uspto-grants-2009_10
Patent number
US07598263B2

Reaction notes

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