HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1042823Generated: October 31, 2026
1-Butanol → 7-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amine
https://huagongshe.com/reaction/1042823
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Butanol | HCID 263 | — |
| Reactant | N-Methyl-4-nitroaniline | HCID 7483 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | 8-Chloro-3-methoxy-1,5-naphthyridine | HCID 59427340 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | 7-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amine | HCID 67317209 | — |
Reaction Steps
To a resealable pressure vessel was added n-methyl-4-nitroaniline (0.911 ml, 7.19 mmol), pyridinium p-toluenesulfonate (1.81 g, 7.19 mmol), 8-chloro-3-methoxy-1,5-naphthyridine (1.000 g, 5.14 mmol), and n-BuOH (15 mL). The vessel was sealed and heated to 100° C. After 4 h, the mixture was cooled to RT, diluted with 1 N NaOH, and extracted with EtOAc. The organic fraction was dried with Na2SO4, concentrated in vacuo, and purified by silica gel chromatography using 50-100% Hexanes:EtOAc to afford 7-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amine as a yellow solid. [email protected] min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08557816B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-149101b1757b4709901e026ab61efc22 |
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| Source note | uspto-grants-2013_10 |
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