Dimethylformamide → HCID 19848792, compound

HRID 2118913Notes

Reaction equation

HRID 2118913 reaction equation
[H-].[K+].CO[C:5]1[CH:10]=[C:9]([CH2:11]NCCCNCCCCNCCCN)[CH:8]=[CH:7][C:6]=1O.O[N:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH:39]([CH2:41][CH2:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH3:40])[CH:36]=2)[C:31](=[O:50])[CH2:30][CH:29]1[CH3:51].[CH2:52](Br)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.CN(C)C=[O:63]>>[CH2:52]([N:28]1[C:37]2[C:32](=[C:33]([O:63][CH2:11][C:9]3[CH:10]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:34]=[C:35]([O:38][CH:39]([CH2:41][CH2:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH3:40])[CH:36]=2)[C:31](=[O:50])[CH2:30][CH:29]1[CH3:51])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide3×HCID 7498Benzyl BromideHCID 82127Potassium hydrideHCID 131714015HCID 131714015, compound

Product 1

HCID 19848792HCID 19848792, compound

Conditions

Temperature
0 °C

Procedure

To a mixture of 0.30 mole of potassium hydride and 500 ml freshly distilled N,N-dimethylformamide (DMF) cooled to 0° C. under nitrogen and anhydrous conditions, is added dropwise a solution of 33.9 g (0.10 mole) dl-5-hydroxy-2-methyl-7-(5-phenyl-2-pentyloxy)-4-oxo-1,2,3,4-tetrahydroquinoline in 350 ml of purified DMF at 0°-10° C. When the addition is complete, the mixture is allowed to warm to room temperature and stirred for one hour. The mixture is then cooled to 0° C., a solution of 18.81 g (0.11 mole) benzylbromide in 150 ml DMF is added slowly at 0°-10° C., the resulting mixture stirred at 5° C. for 30 minutes, then allowed to warm to room temperature and stirred overnight. The reaction is quenched by cautious addition of water, diluted with five liters ethyl ether, washed with water, brine, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo to obtain the crude product. It is purified, if desired, by column chromatography on silica gel.

Workup

  1. additionWhen the addition
  2. temperatureto warm to room temperature
  3. temperatureThe mixture is then cooled to 0° C.
  4. stirringthe resulting mixture stirred at 5° C. for 30 minutes
  5. temperatureto warm to room temperature
  6. stirringstirred overnight
  7. customThe reaction is quenched by cautious addition of water
  8. additiondiluted with five liters ethyl ether
  9. washwashed with water, brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-d043772ded4247cebc4b8c134cf1487d
Source dataset
uspto-grants-1987_07
Patent number
US04680404

Reaction notes

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