N-bromobutanimide → 1633014-63-7

HRID 712772Notes

Reaction equation

HRID 712772 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][NH:7]2.[Br:12]N1C(=O)CCC1=O>C(Cl)Cl>[Br:12][C:11]1[C:2]([Cl:1])=[C:3]2[C:8](=[N:9][CH:10]=1)[NH:7][CH2:6][CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 585167685-chloro-1,2,3,4-tetrahydro-1,8-naphthyridine

Product 1

HCID 1176677451633014-63-7Yield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-1,2,3,4-tetrahydro-[1,8]naphthyridine (500 mg, 3.0 mmol) in DCM (40 mL) is added N-bromosuccinimide (530 mg, 3.0 mmol). The reaction mixture is stirred at room temperature for 2 hrs. The reaction mixture is concentrated to give the crude product. Purification by flash column chromatography affords 680 mg of 6-bromo-5-chloro-1,2,3,4-tetrahydro-[1,8]naphthyridine.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customto give the crude product
  3. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-518f038ee1934b28962cb8c8181f76ef
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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