HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 4,5-Diamino-3-chloro-2-phenylamino-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Ethanol, mixt. with methanol | HCID 18681192 | — |
| Reactant | 4-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester | HCID 85868196 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofurane dichloromethane | HCID 21919333 | — |
| Product | 4,5-Diamino-3-chloro-2-phenylamino-benzoic acid methyl ester | HCID 85868198 | 70.8% |
Reaction Steps
4-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester 5c (0.50 g, 1.55 mmol) is dissolved into 2:1 EtOH/MeOH (15.5 mL). Saturated aqueous NH4Cl (15 mL), Zn powder (1.02 g, 15.6 mmol), and THF (10 mL) are added. After stirring for 20 hours, the reaction mixture is diluted with CH2Cl2/THF and water. The organic layer is washed with water (3×). The combined organic extracts are dried (Na2SO4) and concentrated under reduced pressure. The solids are triturated with ether to give 0.32 g (70%) clean desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07576114B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-c8dfcba554244baeaa79a4ec98de0627 |
| Source note | uspto-grants-2009_08 |