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Water → 3-Amino-4-[methyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]benzonitrile

HRID 2233071
Notes
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Reaction equation

HRID 2233071 reaction equation
[CH3:1][N:2]([C:14]1[CH:23]=[CH:22][C:21]2[C:20]([CH3:25])([CH3:24])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=2[CH:15]=1)[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[N+:11]([O-])=O.[OH-].[Na+].O>CCOC(C)=O>[NH2:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[N:2]([CH3:1])[C:14]1[CH:23]=[CH:22][C:21]2[C:20]([CH3:24])([CH3:25])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=2[CH:15]=1)[C:7]#[N:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 684649384-[Methyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]-3-nitrobenzonitrile

Product 1

HCID 684670903-Amino-4-[methyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]benzonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl Acetate
Solvent
2×

Conditions

Temperature
80 °C

Procedure

SnCl2-2H2O (0.17 mol) is added to a solution of 4-[methyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]-3-nitrobenzonitrile (31) (R4=CH3, 34.0 mmol) in EtOAc (125 mL) and the mixture is heated at 80° C. for 1 h. After cooling, to the reaction mixture are successively added 6N NaOH (120 mL), H2O (150 mL), and EtOAc (150 mL). The reaction mixture is filtered through Celite (25 g) and washed with EtOAc. The organic layer is dried over MgSO4 and evaporated in vacuo. The resulting solid is washed with hexane to give (32) (R4=CH3).

Workup

  1. temperatureAfter cooling, to the reaction mixture
  2. filtrationThe reaction mixture is filtered through Celite (25 g)
  3. washwashed with EtOAc
  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-5216943c3a334fff8314a05d3cbcf181
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709470B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes