Hydrogen Bromide → 3-Bromo-5-methoxyquinoline

HRID 1011431Notes

Reaction equation

HRID 1011431 reaction equation
C(OC(N[C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[C:16]([O:19][CH3:20])[CH:15]=[CH:14][CH:13]=2)=O)(C)(C)C.N([O-])=O.[Na+].C(Cl)Cl.[BrH:28]>O>[Br:28][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[C:16]([O:19][CH3:20])[CH:15]=[CH:14][CH:13]=2

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 23159792HCID 23159792, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 231597643-Bromo-5-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-(tert-butoxycarbonylamino)-5-methoxyquinoline (2.74 g, 10 mmol) in aqueous 48% HBr (40 mL), NaNO2 (2.1 g, 30 mmol) in water (20 mL) is added at 0° C. The reaction mixture is stirred 1 hour. The reaction mixture is extrated with CH2Cl2 (3×30 mL). After drying over MgSO4, dichloromethane is evaporated affording the title compound.

Workup

  1. dry with materialAfter drying over MgSO4, dichloromethane
  2. customis evaporated

Sources & evidence

ORD record
ord-0a7235043210453abccd5a2db4138344
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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