Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | (4-Methoxyphenyl)hydrazine | HCID 77023 | — |
| Reactant | Methyl 2-cyano-4,4-dimethoxybutanoate | HCID 14093058 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 14093060 | HCID 14093060 | 40.3% |
Reaction Steps
A vigorously stirred suspension of para-methoxyphenylhydrazine chlorhidrate (6.47 g, 0.037 mole) in 260 ml of tetrahydrofuran was heated to 67° C. under an argon atmosphere. Compound IV, prepared above (10 g, 0.054 mole)was added at once and a solution of 12 ml of 10N hydrochloric acid in 70 ml of tetrahydrofuran was added over a period of 10 minutes. The reaction mixture was heated at reflux temperature for 35 minutes and further treated as described in Example 3. After chromatography on Silica gel 62 with hexane-ethyl acetate (3:1 v:v) solvent and evaporation of the solvent in vacuo, the viscous oily residue was crystallized from chloroform-hexane to yield 3.65 g (40.3%) of product mp 98°-100° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04803284 |
|---|
| Source dataset | uspto-grants-1989_02 |
|---|
| ORD ID | ord-31fc4518d157485681f3e78218c4d352 |
|---|
| Source note | uspto-grants-1989_02 |
|---|