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

HRID 2233071Notes

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]

Participants

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

temperatureAfter cooling, to the reaction mixture
filtrationThe reaction mixture is filtered through Celite (25 g)
washwashed with EtOAc
dry with materialThe organic layer is dried over MgSO4
customevaporated in vacuo
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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