Hydrochloric Acid → HCID 178515143, compound

HRID 853706

Reaction equation

HRID 853706 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][CH2:12][C:11]2=[O:16])=[CH:4][CH:3]=1.C[O:18][C:19]([C:21]1[C:26]([C:27](OC)=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=1)=O.[H-].[Na+].Cl>O1CCCC1.C(OCC)C.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[C:13]3[C:19]([OH:18])=[C:21]4[C:26]([CH:25]=[CH:24][CH:23]=[N:22]4)=[C:27]([OH:28])[C:12]=3[C:11]2=[O:16])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 690582,3-Dimethyl 2,3-pyridinedicarboxylateHCID 589289521-[2-(4-Fluoro-phenyl)-ethyl]-pyrrolidine-2,5-dione

Product 1

HCID 178515143HCID 178515143, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To 1-[2-(4-Fluoro-phenyl)-ethyl]-pyrrolidine-2,5-dione 309 (270 mg, 1.22 mmol and pyridine-2,3-dicarboxylic acid dimethyl ester (261.6 mg, 1.34 mmol) dissolved in tetrahydrofuran (12.0 ml) and methanol (1.4 ml) was added a 60% dispersion of sodium hydride in mineral oil (108 mg, 2.7 mmol). The reaction mixture was warmed to 80° C. and kept at 80° C. with stirring overnight. The reaction mixture was then placed in an ice bath and titrated to a pH of 4 with 1 M HCl. Two hundred (200) ml of diethylether was then added and the resulting yellow solid was collected by filtration. The solid was washed twice with ether, twice with water, and dried under high vacuum with heating to provide 7-[2-(4-fluoro-phenyl)-ethyl]-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione 310 (250 mg, 0.71 mmol, 58%). 1H NMR (d-DMSO) δ 10.7 (broad, 1H), 8.98 (dd, 1H), 8.66 (dd, 1H), 7.73 (m, 1H), 7.18 (m, 2H), 7.04 (t, 2H), 3.72 (t, 2H), 2.86 (t, 2H). MS: 353.1 (M+1).

Workup

  1. customkept at 80° C.
  2. customThe reaction mixture was then placed in an ice bath
  3. filtrationthe resulting yellow solid was collected by filtration
  4. washThe solid was washed twice with ether, twice with water
  5. customdried under high vacuum
  6. temperaturewith heating

Sources & evidence

ORD record
ord-9803244f792e4dc5b3604b85b4a2777d
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Linked notes

Loading…