Sodium Chloride → 2-(4,5-Dichloroquinolin-2-yl)-2,3,4,5-tetrahydro-1H-2-benzazepine

HRID 540314Notes

Reaction equation

HRID 540314 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](N)=[CH:5][C:6]([N:12]1[CH2:18][CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[CH2:13]1)=[N:7]2.N([O-])=O.[Na+].[Cl-:28].[Na+].C(=O)(O)[O-].[Na+]>Cl.O>[Cl:28][C:4]1[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[Cl:1])[N:7]=[C:6]([N:12]2[CH2:18][CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[CH2:13]2)[CH:5]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 712553505-Chloro-2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-amine

Product 1

HCID 712551482-(4,5-Dichloroquinolin-2-yl)-2,3,4,5-tetrahydro-1H-2-benzazepine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To the suspension of 5-chloro-2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-amine (1.5 g, 4.6 mmol) in concentrated hydrochloric acid (10 mL) was added a solution of sodium nitrite (390 mg, 5.6 mmol) in water at −10° C. After the addition, the reaction mixture was stirred for further 30 minutes, and then sodium chloride (2 g) was added. The resulting mixture was stirred at room temperature overnight and neutralized with saturated sodium bicarbonate, extracted with dichloromethane (50 mL×2). The organic layers were combined and dried over sodium sulfate, and then concentrated under reduced pressure to give the crude product. It was used in next step without further purification.

Workup

  1. additionAfter the addition
  2. extractionextracted with dichloromethane (50 mL×2)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e662845b6934424e8f797ae02abf6b76
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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