Dimethylformamide → 4-[Methyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]-3-nitrobenzonitrile

HRID 2233070Notes

Reaction equation

HRID 2233070 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[NH:14][C:15]1[CH:24]=[CH:23][C:22]2[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=2[CH:16]=1)[C:9]#[N:10])([O-:5])=[O:4].[CH3:29]N(C=O)C>O>[CH3:29][N:14]([C:15]1[CH:24]=[CH:23][C:22]2[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=2[CH:16]=1)[C:13]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[N+:3]([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 592951013-Nitro-4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylamino)benzonitrile

Product 1

HCID 684649384-[Methyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]-3-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaH (60%, 6.44 mmol) is added portionwise to a solution of 3-nitro-4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylamino)benzonitrile (30, R4=CH3, 4.29 mmol) in DMF (15 mL) at 0° C. The reaction mixture is slowly warmed up to room temperature and stirred for 1 h. To the mixture is added dropwise Mel (6.44 mmol) and the reaction mixture is stirred at room temperature for 5 h. The mixture is diluted with H2O and extracted with Et2O. The organic layer is dried over MgSO4 and evaporated in vacuo. The resulting solid is washed with hexane to give (31) (R4=CH3).

Workup

  1. additionTo the mixture is added dropwise Mel (6.44 mmol)
  2. stirringthe reaction mixture is stirred at room temperature for 5 h
  3. extractionextracted with Et2O
  4. dry with materialThe organic layer is dried over MgSO4
  5. customevaporated in vacuo
  6. washThe resulting solid is washed with hexane

Sources & evidence

ORD record
ord-bf88354a29334fe597d82d84d6b832c1
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

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