Sodium Hydroxide → HCID 57471196, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16]C)[CH:14]=2)[CH2:9][CH2:8][CH:7]1[NH2:18].[OH-].[Na+]>ClCCl>[NH2:18][CH:7]1[CH:6]([CH2:5][C:4]2[CH:19]=[CH:20][C:21]([Cl:22])=[C:2]([Cl:1])[CH:3]=2)[C:15]2[CH:14]=[C:13]([OH:16])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
1-(3,4-Dichlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine (10 g, 26.8 mmol, cf. example 3.2 were dissolved in dichloromethane (240 mL). The suspension was cooled to −10° C. and a 1 M solution of bortribromide in dichloromethane (80 mL, 80 mmol). The solution was allowed to warm to room temperature and stirring was continued for 3 h. The reaction mixture was poured on ice (1 L). The aqueous layer was made alkaline (pH 10) with 2N sodium hydroxide solution. The layers were separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed with saturated NaHCO3 solution and water. The organic layers were dried (Na2SO4) and concentrated in vacuo. The crude product was used without further purification for the next step. Yield: 10.8 g
Workup
- temperatureto warm to room temperature
- additionThe reaction mixture was poured on ice (1 L)
- customThe layers were separated
- extractionThe aqueous layer was extracted with dichloromethane
- washthe combined organic layers were washed with saturated NaHCO3 solution and water
- dry with materialThe organic layers were dried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe crude product was used without further purification for the next step
Sources & evidence
- ORD record
- ord-b156b9f320484ab281c55706bdd7f9a4
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563617B2
Reaction notes
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