Dimethylformamide → HCID 492949, compound

HRID 1032719Notes

Reaction equation

HRID 1032719 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[CH:16]=3)[C:11](=[O:24])[C:10]([C:25]([NH2:27])=[O:26])=[CH:9]2)=[CH:4][CH:3]=1.[Cl-].[CH2:29]=[N+:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.CN(C=O)C.C(=O)(O)[O-].[Na+]>O>[N:30]1([CH2:29][NH:27][C:25]([C:10]2[C:11](=[O:24])[C:12]3[C:17](=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[CH:14][CH:13]=3)[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:9]=2)=[O:26])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 443370HCID 443370, compoundHCID 516892Sodium BicarbonateHCID 11367014Morpholinium, 4-methylene-, chloride

Product 1

HCID 492949HCID 492949, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.08 g 1-(4-fluorophenyl)-1,4-di -hydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxamide (Example 1 h), 0.45 g N-methylenemorpholinium chloride and 10 ml DMF was heated at 100° C. for 15 min. The reaction mixture was cooled, poured into 100 ml water and the pH adjusted to 8 with saturated sodium bicarbonate solution. The solid precipitate was collected, dried and recrystallized from an acetonitrile -chloroform mixture to give 0.90 g N-(4-morpholinylmethyl)-1-(4-fluorophenyl)1,4 -dihydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxamide, m.p. 258-260° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe solid precipitate was collected
  3. customdried
  4. customrecrystallized from an acetonitrile -chloroform mixture

Sources & evidence

ORD record
ord-d4796169f85e4e5fb59f8bb67dfcf2ea
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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