Pyridine → HCID 21699665, compound

HRID 1597283Notes

Reaction equation

HRID 1597283 reaction equation
[NH2:1][C:2]1[C:11]2[CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7][C:6]=2[N:5]=[C:4]2[CH:19]=[CH:20][CH:21]=[CH:22][C:3]=12.N1C=CC=CC=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>O>[C:15]([O:14][C:12]([N:9]1[CH2:8][CH2:7][C:6]2[N:5]=[C:4]3[CH:19]=[CH:20][CH:21]=[CH:22][C:3]3=[C:2]([NH:1][C:29](=[O:31])[CH3:30])[C:11]=2[CH2:10]1)=[O:13])([CH3:17])([CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21699658HCID 21699658, compound

Product 1

HCID 21699665HCID 21699665, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10-Amino-2-t-butoxycarbonyl-1,2,3,4-tetrahydro-benzo[b][1,6]-naphthyridine (0.77 g, 2.59 mmol) was added to pyridine (1.0 g, 12.7 mmol). Acetic anhydride (0.53 g, 5.18 mmol) was added to the mixture, followed by refluxing for 7.5 hours. Then, water was added thereto and the resulting mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by a silica gel column chromatography to obtain the desired compound (0.5 g, 1.47 mmol, 57%).

Workup

  1. temperatureby refluxing for 7.5 hours
  2. extractionthe resulting mixture was extracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-ec04908115324944932c7067681e5f74
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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