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Dimethylformamide → 10-(((dimethylamino)ethyl)thio)-8-hydroxy-11H-indeno[1,2-b]quinolin-11-one

HRID 963256
Notes
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Reaction equation

HRID 963256 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[C:13]3[C:18]([C:19](=[O:20])[C:3]=12)=[CH:17][CH:16]=[CH:15][CH:14]=3.C(=O)([O-])[O-].[Li+].[Li+].Cl.[CH2:28]([N:30]([CH2:34]C)[CH2:31][CH2:32][SH:33])C.CN(C)C=O>O>[CH3:28][N:30]([CH2:31][CH2:32][S:33][C:2]1[C:11]2[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[C:13]3[C:18]([C:19](=[O:20])[C:3]=12)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11125Lithium CarbonateHCID 16031Ethanethiol, 2-(diethylamino)-, hydrochloride (1:1)HCID 1908181510-chloro-8-hydroxy-11H-indeno[1,2-b]quinolin-11-one

Product 1

HCID 2244020810-(((dimethylamino)ethyl)thio)-8-hydroxy-11H-indeno[1,2-b]quinolin-11-oneYield 63.2%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 400 mg (1.4 mmol) of 10-chloro-8-hydroxy-11H-indeno[1,2-b]quinolin-11-one, 629 mg (8.5 mmol) of lithium carbonate, 963 mg (5.7 mmol) of 2-diethylaminoethanethiol hydrochloride and 8 ml of N,N-dimethylformamide was stirred for 5 hours with heating at 90° C. After completion of the reaction, the reaction mixture was added to water, and precipitated crystals were collected by filteration. The crystals were recrystallized from ethanol, giving 310 mg of the title compound (yield: 57.7%). The property values are shown in Table 1.

Workup

  1. customAfter completion of the reaction
  2. customprecipitated crystals
  3. customwere collected by filteration
  4. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-f77d3e454a19410ba31af60dc53a8981
Source dataset
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05763453

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes