Water → HCID 178481484, compound

HRID 1739818Notes

Reaction equation

HRID 1739818 reaction equation
[C:1]([N:3]=[CH:4]OCC)#[N:2].[NH2:8][CH:9]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=[C:13]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O.C(OCC)(=O)C>C(O)C>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([CH:9]([NH:8][CH:4]=[N:3][C:1]#[N:2])[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=[C:13]3[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9920370Methanimidic acid, N-cyano-, ethyl esterHCID 21837488(+/-)-6-[amino-(4-chlorophenyl)methyl]-1-methyl-4-phenyl-2(1H)-quinolinone

Product 1

HCID 178481484HCID 178481484, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-cyano-methanimidate (3.6 g) was added dropwise at room temperature to a solution of intermediate (5-b) (10.6 g) in ethanol (90 ml) and the mixture was stirred at room temperature for 48 hours. Water and ethyl acetate were added, the organic layer was decanted, washed with water, dried (MgSO4), filtered off and evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 97/3/0.1). The pure fractions were collected and evaporated, yielding 10.5 g (88%) of (±)-N-[[[(4-chlorophenyl)(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)methyl]amino]methylene]cyanamide (interm. 5-c).

Workup

  1. customthe organic layer was decanted
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered off
  5. customevaporated till dryness
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 97/3/0.1)
  7. customThe pure fractions were collected
  8. customevaporated

Sources & evidence

ORD record
ord-d86fb029408b488298f1afd5c238e640
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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