Water → HCID 82580922, compound

HRID 1772172Notes

Reaction equation

HRID 1772172 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][CH:15]=[C:14]2[CH3:21].O.[OH-].[Na+]>S(=O)(=O)(O)O>[Br:1][C:12]1[C:11]([O:10][CH3:9])=[CH:20][CH:19]=[C:18]2[C:13]=1[C:14]([CH3:21])=[CH:15][CH:16]=[N:17]2

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 2587616-Methoxy-4-methylquinoline

Product 1

HCID 82580922HCID 82580922, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-bromosuccinimide (0.57 g, 3.2 mmol) is added at RT to a mixture of 6-methoxy-4-methylquinoline (0.5 g, 2.9 mmol) in conc. sulfuric acid (5 ml). The mixture is stirred for 1 h and poured onto ice-water. The water phase is made basic with an aqueous solution of sodium hydroxide (1 mol/l) and extracted with DCM. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 256 mg (35%). HPLC-MS: M+H=252/254; tR=1.09 min (METHOD—1).

Workup

  1. additionpoured onto ice-water
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-84ab2aae7c9a4e69b63f4ddff6c86622
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

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