Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethyl Sulfate | HCID 6497 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 4,5-Dimethyl-2-nitrobenzenamine | HCID 81445 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 601943 | HCID 601943 | 69.4% |
Reaction Steps
A solution of 4,5-dimethyl-2-nitroaniline (2.00 g, 12 mmol) in toluene (25 mL) was added NaOH (1.93 g, 48 mmol). The reaction mass was stirred at 100° C. for 1 h, followed by addition of dimethyl sulphate (4.6 g, 36 mmol) and reaction mass was stirred at RT for 24 h. The reaction mass was quenched in water, extracted with DCM and concentrated to afford 1.5 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 2.11 (s, 3H), 2.24 (d, J=7.8 Hz, 3H), 2.92 (s, 3H), 6.77 (m, 1H), 7.79 (m, 1H), 8.06 (s, 1H); MS (m/z): 180.92 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09096545B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-1a395de7403f43f28256c444554cafc0 |
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| Source note | uspto-grants-2015_08 |
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