Hydrogen chloride-ethyl acetate → 1,3,4,5-tetrahydrobenzo[c]-1,7-naphthyridin-6(2H)-one

HRID 1670752Notes

Reaction equation

HRID 1670752 reaction equation
C(OC([N:8]1[CH2:17][C:16]2[NH:15][C:14](=[O:18])[C:13]3[CH:19]=[CH:20][CH:21]=[CH:22][C:12]=3[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(OCC)(=O)C>O1CCCC1>[CH2:10]1[CH2:9][NH:8][CH2:17][C:16]2[NH:15][C:14](=[O:18])[C:13]3[CH:19]=[CH:20][CH:21]=[CH:22][C:12]=3[C:11]1=2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67342213HCID 67342213, compound

Product 1

HCID 99737611,3,4,5-tetrahydrobenzo[c]-1,7-naphthyridin-6(2H)-oneYield 117.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

6-Oxo-1,4,5,6-tetrahydrobenzo[c]-1,7-naphthyridine-3(2H)-carboxylic acid tert-butyl ester (1.13 g) was added to tetrahydrofuran (30 ml) and dissolved by stirring the mixture at 60° C. 4N Hydrochloric acid-ethyl acetate (20 ml) was added, and the mixture was stirred with heating at 60° C. for 1 hr. The reaction mixture was ice-cooled, and the precipitated solid was collected by filtration, washed with ethyl acetate and dried to give 1,3,4,5-tetrahydrobenzo[c]-1,7-naphthyridin-6(2H)-one (884 mg, yield 90%).

Workup

  1. dissolutiondissolved
  2. stirringthe mixture was stirred
  3. temperaturewith heating at 60° C. for 1 hr
  4. temperaturecooled
  5. filtrationthe precipitated solid was collected by filtration
  6. washwashed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-208c6ba109f64cdbb2319fab3d36ee13
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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