Nitric Acid → HCID 11579837, compound

HRID 853884Notes

Reaction equation

HRID 853884 reaction equation
[Cl:1][C:2]1[CH:3]=[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.[N+:16]([O-])([OH:18])=[O:17]>OS(O)(=O)=O>[Cl:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[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

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 14181388HCID 14181388, compound

Product 1

HCID 11579837HCID 11579837, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

To a cold mixture of 7-chloro-3,4-dihydropyrimido[1,2-a]indole-10(2H)-one (0.221 g, 1.00 mmol ) in concentrated H2SO4 (1 mL), was added fuming nitric acid (0.042 mL, 1.00 mmol ) drop-wise with cooling in a ice/brine bath (−10° C.). After stirring for 10 minutes the ice bath was removed and stirring continued for 1 hour at room temperature. Controlling the temperature with an ice bath, fresh fuming HNO3 (0.021 mL) was added. After stirring for an additional hour the mixture was added to ice and basified with concentrated NH4OH. The resulting yellow solid was filtered, dissolved in CH2Cl2 and filtered again. The filtrate was washed with H2O and the organic layer was separated and concentrated to give the title compound as a bright yellow solid (0.209 g, 79% yield). Anal. Calc'd for C11H8ClN3O3+0.2H2O: C, 47.60; H, 3.00; N, 14.87. Found: C, 47.58; H, 3.02; N, 14.85. NMR (300 Mz, DMSO-d6): consistent. MS: (ES+) m/z 266 [M+H] one chlorine pattern observed. m.p.: 152-165° C.

Workup

  1. customwas removed
  2. additionfresh fuming HNO3 (0.021 mL) was added
  3. stirringAfter stirring for an additional hour the mixture
  4. additionwas added to ice and basified with concentrated NH4OH
  5. filtrationThe resulting yellow solid was filtered
  6. dissolutiondissolved in CH2Cl2
  7. filtrationfiltered again
  8. washThe filtrate was washed with H2O
  9. customthe organic layer was separated
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5ed6633364db4506aee8f66c3bed975e
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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