Sodium hydride → HCID 22113088, compound

HRID 564955Notes

Reaction equation

HRID 564955 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[CH:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CS(O[CH2:27][C:28]1[C:33]([Cl:34])=[CH:32][CH:31]=[C:30]([N+:35]([O-:37])=[O:36])[C:29]=1[Cl:38])(=O)=O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[CH:14]2)[CH2:27][C:28]1[C:33]([Cl:34])=[CH:32][CH:31]=[C:30]([N+:35]([O-:37])=[O:36])[C:29]=1[Cl:38])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10566104HCID 10566104, compoundHCID 15527049HCID 15527049, compound

Product 1

HCID 22113088HCID 22113088, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-tert-butoxycarbonylamino-2-methylquinoline (258 mg) in N,N-dimethylformamide (3 ml) was added sodium hydride (44 mg) in an ice-water bath cooling, and the mixture was stirred for 20 minutes at the same temperature. To the reaction mixture was added 2,6-dichloro-3-nitrobenzyl methanesulfonate (300 mg) in an ice water bath cooling, and the mixture was stirred for 80 minutes at the same temperature and then for 15 minutes at ambient temperature. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography eluting with methylene chloride, and crystallized with n-hexane to give 8-[N-tert-butoxycarbonyl-N-(2,6-dichloro-3-nitrobenzyl)amino]-2-methylquinoline (352 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 80 minutes at the same temperature
  4. waitfor 15 minutes at ambient temperature
  5. customThe reaction mixture was partitioned between ethyl acetate and water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography
  9. washeluting with methylene chloride
  10. customcrystallized with n-hexane

Sources & evidence

ORD record
ord-b1707a893a4843b09a4c50482a0b3b1c
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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