Water → HCID 14423300, compound

HRID 1197031Notes

Reaction equation

HRID 1197031 reaction equation
CC1(C)CO[C:5]2([CH2:27][CH2:26][C:10]3[N:11]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:12]4[N:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:18](=[O:19])[C:9]=3[CH2:8]2)[O:4]C1.O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(=O)CC>[C:20]1([N:11]2[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18](=[O:19])[C:9]3[CH2:8][C:5](=[O:4])[CH2:27][CH2:26][C:10]2=3)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 14423237HCID 14423237, compound

Product 1

HCID 14423300HCID 14423300, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Reflux 6,8,9,10-tetrahydro-5',5'-dimethyl-10-phenyl-spiro[benzo[b][1,8]naphthyridin-7-(5H),2'-[1,3]dioxan]-5-one (32 mmoles) with water (6 ml) and p-toluenesulfonic acid monohydrate (3.2 g) dissolved in 2-butanone (319 ml) for 3 days. Monitor the progress of hydrolysis by thin-layer chromatography. When hydrolysis is complete, cool the solution and evaporate the 2-butanone. Wash a CH2Cl2 solution of the residue with aqueous NaHCO3 solution and with water. Evaporate the CH2Cl2 after drying the organic solution, and crystallize the residue from C2H5OH--CHCl3 to obtain 6,8,9,10-tetrahydro-10-phenyl-benzo[b][1,8]naphthyridin-5,7-dione, m.p. 244°-247° C. (d).

Workup

  1. customMonitor the progress of hydrolysis by thin-layer chromatography
  2. customWhen hydrolysis
  3. temperaturecool the solution
  4. customevaporate the 2-butanone
  5. washWash a CH2Cl2 solution of the residue with aqueous NaHCO3 solution
  6. customEvaporate the CH2Cl2
  7. customafter drying the organic solution
  8. customcrystallize the residue from C2H5OH

Sources & evidence

ORD record
ord-101fa7b2a8c04f868bc9456e5ff1dacb
Source dataset
uspto-grants-1992_05
Patent number
US05116840

Reaction notes

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