Water → HCID 178439567, compound

HRID 1650096Notes

Reaction equation

HRID 1650096 reaction equation
[C:1]([C:4]([NH:9][C:10]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)=O)([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2].[H-].[Na+].O>C1(C)C(C)=CC=CC=1>[CH:5]([C:4]1([CH3:8])[NH:9][C:10]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[N:2][C:1]1=[O:3])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 13730776HCID 13730776, compound

Product 1

HCID 178439567HCID 178439567, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a slurry of N-(1-carbamoyl-1,2-dimethylpropyl)-2-quinolinecarboxamide (16.04 g, 0.0562 mol) in xylene (610 ml) under nitrogen is added a 50% oil dispersion of sodium hydride (2.7 g, 0.056 mol) at 20° C. The reaction is heated to reflux for 2 hours, cooled and water (50 ml) added. The aqueous layer is extracted with methylene chloride and the organic layers combined and evaporated to give a yellow oil, 17 g. Purification is accomplished by passing through a silica gel column using hexane-ethyl acetate as solvent. A pale yellow solid is obtained and is recrystalized from ethyl acetate to give 11.77 g (78%) of white product, mp 112°-117° C. Anal. calcd. for C16H17N3O: C, 71.88; H, 6.41; N, 15.72. Found: C, 71.91; H, 6.47; N, 15.70.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux for 2 hours
  3. temperaturecooled
  4. extractionThe aqueous layer is extracted with methylene chloride
  5. customevaporated
  6. customto give a yellow oil, 17 g
  7. customPurification
  8. customA pale yellow solid is obtained
  9. customis recrystalized from ethyl acetate

Sources & evidence

ORD record
ord-92432120e37b4c9d8940d798c7223c17
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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