2-Ethylaniline → HCID 54083637, compound

HRID 743109Notes

Reaction equation

HRID 743109 reaction equation
[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1Cl)=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17][CH2:18][S:19][CH3:20])(=[O:4])[CH2:2][CH3:3].[CH2:21]([C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25])[CH3:22]>C(#N)C>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:25][C:24]1[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=1[CH2:21][CH3:22])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17][CH2:18][S:19][CH3:20])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 113572-EthylanilineHCID 54113854HCID 54113854, compound

Product 1

HCID 54083637HCID 54083637, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-propanoyl-4-chloro-8-(2-methylthioethoxy)quinoline (0.093 g, 0.34 mmol) and 2-ethyl aniline (0.048 g, 0.39 mmol) in acetonitrile (1 ml) was heated to 65° C. and stirred 4.0 h. The solvent was evaporated and the residue was partitioned between methylene chloride and a saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate and evaporated. The residue was chromatographed (SiO2 ; ethyl acetate) yielding 40 mg (30%) of the desired product.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed (SiO2 ; ethyl acetate)

Sources & evidence

ORD record
ord-75535dffafa748fa951fb59ff6ba8ffc
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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