HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Nitro-4-chloro-6-methylanisole → 5-Chloro-2-methoxy-3-methylaniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Nitro-4-chloro-6-methylanisole | HCID 22997638 | — |
| Catalyst | Platinum | HCID 23939 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 5-Chloro-2-methoxy-3-methylaniline | HCID 22997657 | 90.3% |
Reaction Steps
A suspension of 2-nitro-4-chloro-6-methylanisole (16 g) and 10% Pt(S)/C (1.6 g) in ethanol was hydrogenated at 50 psi for 3 hours. After filtration and concentration, purification by flash chromatography over silica gel (eluted with 10% ethyl acetate in hexanes) gave 12.3 g (90%) of 2-amino-4-chloro-6-methylanisole. 1H NMR (300 MHz, CDCl3) δ6.58 (d, J=2.4 Hz, 1 H), 6.53 (d, J=2.4 Hz, 1 H), 3.77 (s, 3 H), 2.22 (s, 3 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06613786B2 |
| Source dataset | uspto-grants-2003_09 |
| ORD ID | ord-a6bf4dbab8824843a91118885753762c |
| Source note | uspto-grants-2003_09 |