2-Isopropylaniline → HCID 54241858, compound

HRID 743111Notes

Reaction equation

HRID 743111 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-0437f6df8e1b4be689b7735976f83cbd
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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