Water → HCID 21699684, compound

HRID 1597287Notes

Reaction equation

HRID 1597287 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]3=[C:11](C(N)=O)[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na].BrBr.[OH2:28]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]3=[C:11]([NH:8][C:6]([O:5][CH3:1])=[O:28])[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 5360545SodiumHCID 21699696HCID 21699696, compound

Product 1

HCID 21699684HCID 21699684, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

2-t-Butoxycarbonyl-1,2,3,4-tetrahydro-benzo[b][1,6]-naphthyridine-10-carboxamide (0.5 g, 1.53 mmol) was added to a solution of sodium (0.078 g, 3.37 mmol) in methanol (31 ml), and bromine (0.245 g, 1.53 mmol) was added dropwise thereto while maintaining the temperature at 25° C. or lower. After completion of the dropwise addition, the resulting mixture was heated under reflux for 30 minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue was purified by a silica gel chromatography (hexane-ethyl acetate=1 : 1) to obtain the desired compound (0.46 g, 1.28 mmol, 84%).

Workup

  1. additionwas added dropwise
  2. additionAfter completion of the dropwise addition
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for 30 minutes
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by a silica gel chromatography (hexane-ethyl acetate=1 : 1)

Sources & evidence

ORD record
ord-0346f93c83354f6abbbeff3363382330
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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