Hydrochloric Acid → (+/-)-2'-Oxo-1',2',6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridine]-3-carbaldehyde

HRID 2262847Notes

Reaction equation

HRID 2262847 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.[CH2:20]1C[O:23][CH2:22][CH2:21]1.Cl.[C:26]([O-])(O)=O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[O:15]=[C:7]1[NH:8][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:14]2[C:6]21[CH2:16][C:17]1[CH:18]=[C:19]3[C:2](=[CH:3][C:4]=1[CH2:5]2)[N:1]=[CH:20][C:21]([CH:22]=[O:23])=[CH:26]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2×

Product 1

HCID 59594349(+/-)-2'-Oxo-1',2',6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridine]-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6212ChloroformSolvent

Procedure

(±)-5-Amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (125 mg, 0.500 mmol, described in Intermediate 4) and 2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bis(tetrafluoroborate) (266 mg, 0.750 mmol) were suspended in glacial acetic acid and the mixture was heated to reflux for 22 h. The mixture was allowed to cool to ambient temperature before the bulk of the acetic acid was removed in vacuo. THF (3 mL) and 1 N HCl (3 mL, 3 mmol) were added and the mixture was stirred at ambient temperature for 2 h. The mixture was then poured into a separatory funnel containing CHCl3 (50 mL) and saturated aqueous NaHCO3 (10 mL). The aqueous layer was extracted twice with CHCl3 (2×250 mL) and the combined organic layers were dried over Na2SO4. Filtration to remove drying agent gave a solution which was concentrated in vacuo to give a yellow residue. The impure product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:1 to 92:8, to give the title compound. MS: m/z=316 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 22 h
  3. customwas removed in vacuo
  4. additionThe mixture was then poured into a separatory funnel
  5. extractionThe aqueous layer was extracted twice with CHCl3 (2×250 mL)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationFiltration
  8. customto remove
  9. customdrying agent
  10. customgave a solution which
  11. concentrationwas concentrated in vacuo
  12. customto give a yellow residue
  13. customThe impure product was purified by silica gel chromatography
  14. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-535b9d75cf5c405b879cadaa89cc82c3
Source dataset
uspto-grants-2010_12
Patent number
US07851464B2

Reaction notes

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