Sulfuric Acid → HCID 22759433, compound

HRID 853872Notes

Reaction equation

HRID 853872 reaction equation
OS(O)(=O)=O.[CH3:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH2:19][N:20]=[C:12]3[C:11]3(OCCC[O:21]3)[C:10]=2[CH:9]=1.[NH4+].[OH-]>>[CH3:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH2:19][N:20]=[C:12]3[C:11](=[O:21])[C:10]=2[CH:9]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 58932576HCID 58932576, compound

Product 1

HCID 22759433HCID 22759433, compound

Procedure

To cold concentrated H2SO4 (4 mL) was added 8′-methoxy-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2-a]indole] (0.204 g, 0.744 mmol) portion-wise over a period of 15 minutes with cooling in an ice bath. After stirring for 35 min., the reaction was poured onto ice and basified with concentrated NH4OH keeping the reaction cold with ice. The reaction mixture was extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, and filtered and concentrated. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH (98.5/1/0.5) to give the title compound as a bright red solid. Anal: Calc'd for C12H12N2O2 0.1H2O: C, 66.10; H, 5.64; N, 12.85. Found: C, 65.81; H, 5.28; N, 12.78. NMR (300 Mz, DMSO-d6): consistent. MS: (APCI+) m/z 217[M+H]. m.p.: 152° C.

Workup

  1. temperaturewith cooling in an ice bath
  2. customthe reaction cold with ice
  3. extractionThe reaction mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH (98.5/1/0.5)

Sources & evidence

ORD record
ord-3e22287d9c1443a6a23e0c480223b939
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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