Dimethylformamide → HCID 58932524, compound

HRID 853885Notes

Reaction equation

HRID 853885 reaction equation
[Cl:1][C:2]1[C:3]([N+:16]([O-])=O)=[CH:4][C:5]2[C:6](=[O:15])[C:7]3[N:8]([CH2:11][CH2:12][CH2:13][N:14]=3)[C:9]=2[CH:10]=1.O.O.Cl[Sn]Cl.CN(C=O)C>CCOC(C)=O>[NH2:16][C:3]1[C:2]([Cl:1])=[CH:10][C:9]2[N:8]3[CH2:11][CH2:12][CH2:13][N:14]=[C:7]3[C:6](=[O:15])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 61436Stannous chloride dihydrateHCID 11579837HCID 11579837, compound

Product 1

HCID 58932524HCID 58932524, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of finely ground 7-chloro-8-nitro-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one (0.200 g, 0.753 mmol ) in EtOAc (10 mL) was added SnCl2.2H2O and the mixture was heated at reflux for 1.75 hr after which DMF (2 mL) was added and the reaction proceeded quickly. The reaction was cooled to room temperature and quenched with sat. aq. NaHCO3 (25 mL ). EtOAc (25 mL ) was added and the mixture was stirred for 0.5 hr then filtered. The biphasic layers were separated and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and concentrated. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH (94/4/2) to give the title compound as a black solid (0.029 g, 16% yield). Anal. Calc'd for C11H10ClN3O: C, 56.06% , H, 4.28% ; N, 17.83% . Found: C, 55.81% ; H, 4.17% ; N, 17.54% . NMR (300 Mz, DMSO-d6): consistent. MS: (ES−) 238 [M−H]. m.p.>270° C.

Workup

  1. temperaturethe mixture was heated
  2. additionwas added
  3. customquenched with sat. aq. NaHCO3 (25 mL )
  4. additionEtOAc (25 mL ) was added
  5. filtrationthen filtered
  6. customThe biphasic layers were separated
  7. extractionthe aqueous layer was extracted with EtOAc
  8. dry with materialThe combined organic extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH (94/4/2)

Sources & evidence

ORD record
ord-d6f11a86f6714cb999168734e2de95f5
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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