2-Isopropylaniline → HCID 54241858, compound

HRID 1419865Notes

Reaction equation

HRID 1419865 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].[CH:21]([C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26])([CH3:23])[CH3:22]>C(#N)C>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:26][C:25]1[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=1[CH:21]([CH3:23])[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 125612-IsopropylanilineHCID 54113854HCID 54113854, compound

Product 1

HCID 54241858HCID 54241858, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-propanoyl-4-chloro-8-(2-methylthioethoxy)quinoline (305 mg, 1 mmol) and 2-isopropylaniline (1 ml) in 25 ml acetonitrile was refluxed overnight. 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 on a prep-TLC (methylene chloride:ethyl acetate 1:1) yielding 30 mg (8%) of the desired product.

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on a prep-TLC (methylene chloride:ethyl acetate 1:1)

Sources & evidence

ORD record
ord-6b1e3c577b36483eb3848e25eabdd030
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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