N-bromobutanimide → HCID 9977862, compound

HRID 1672346Notes

Reaction equation

HRID 1672346 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[CH:13][N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1.[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:22][C:13]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[C:5]2[C:4]3[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:12]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10448328HCID 10448328, compound

Product 1

HCID 9977862HCID 9977862, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2 g (6.36 mmol) of 8-chloro-1-(2-chloro-phenyl)-1H-imidazo[4,5-c]quinoline (Example 25), 6.6 g (37 mmol) N-bromosuccinimide, and 1.32 g (4.45 mmol) FeBr3 (98%; Aldrich) are heated and kept under reflux during 2½ h in 50 ml CHCl3. The cold solution is poured on ca. 300 ml ice-water, where a precipitate is formed. Extraction of the water phase with CH2Cl2 and chromatography of the raw material on silicagel (hexane-ethyl acetate 1:1) gives the desired title compound. mp: 183-192° C.; MS: 392 (M++1); HPLC: tret=12.44 min (Grad 1).

Workup

  1. customis formed
  2. extractionExtraction of the water phase with CH2Cl2 and chromatography of the raw material on silicagel (hexane-ethyl acetate 1:1)

Sources & evidence

ORD record
ord-a68afa1febfe4c02bfc525cee043cdba
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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