Nitric Acid → HCID 67492871, compound

HRID 1922383Notes

Reaction equation

HRID 1922383 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[C:3]1=[O:18].OS(O)(=O)=O.[N+:24]([O-])([OH:26])=[O:25]>>[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:24]([O-:26])=[O:25])[CH:9]=2)[N:4]([CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[C:3]1=[O:18]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 67492670HCID 67492670, compound

Product 1

HCID 67492871HCID 67492871, compoundYield 61%

Procedure

A solution of 3-methyl-1-(1-methylpiperidin-4-yl)indolin-2-one(0.18 g, 0.736 mmol) in con. H2SO4 (2 mL) was treated with fuming HNO3 (0.034 mL, 0.736 mmol) at −5 to −10° C. (ice+salt) and resulting solution was stirred for 30 min. at this same temperature. The reaction was quenched with addition of crushed ice, and then basified with 1 N NaOH and product was extracted into CH2Cl2 (2×20 mL). The combined CH2Cl2 layer was washed with brine (10 mL) and dried (Na2SO4). The solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5) to obtain compound 3-methyl-1-(1-methylpiperidin-4-yl)-5-nitroindolin-2-one (0.13 g, 61%) as a solid. 1H NMR (DMSO-d6) δ: 1.39 (d, 3H, J=7.5 Hz), 1.55-1.62 (m, 2H), 2.01 (t, 2H, J=11.4 Hz), 2.20 (s, 3H), 2.31-2.39 (m, 2H), 2.87 (d, 2H, J=11.4 Hz), 3.63 (q, 1H), 4.06-4.16 (m, 1H), 7.39 (d, 1H, J=9.3 Hz), 8.18-8.22 (m, 2H); ESI-MS (m/z, %) 290 (MH+, 100).

Workup

  1. customresulting solution
  2. customThe reaction was quenched with addition of crushed ice
  3. extractionwas extracted into CH2Cl2 (2×20 mL)
  4. washThe combined CH2Cl2 layer was washed with brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated
  7. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5)

Sources & evidence

ORD record
ord-8542dd4f8eee4237b8f1a074d3ba986d
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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