Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | HCID 69811588 | HCID 69811588 | — |
| Catalyst | Adams' catalyst | HCID 345198 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86651536 | HCID 86651536 | — |
Reaction Steps
A suspension of (A5) and PtO2 (0.1 eq.) in a solvent mixture of HCO2H (80% sol. in water)/THF=2.5:1 (0.2 M) was heated to 60° C. for 4 h. After cooling, the catalyst was filtered through a pad of celite, then, the solvent was reduced in vacuo and the residue partioned between sat. aq. NaHCO3 and DCM. The aqueous phase was separated and extracted several times with DCM. The combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent gave the title compound which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3, 300K) δ 9.96 (1H, s), 7.78 (2H, d, J=7.8 Hz), 7.85-7.78 (3H, m), 7.72 (1H, d, J=8.6 Hz), 7.29 (1H, d, J=7.8 Hz), 7.27-7.18 (1H, m), 6.50-6.40 (2H, m), 4.78 (2H, s), 3.79 (3H, s), 3.75 (3H, s), 3.70-3.60 (2H, m), 3.30-3.20 (2H, m). MS (ES+) C26H23N3O4 requires: 441, found: 442 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08362030B2 |
|---|
| Source dataset | uspto-grants-2013_01 |
|---|
| ORD ID | ord-14f3481c9afd4bacba58a6ad1d861b63 |
|---|
| Source note | uspto-grants-2013_01 |
|---|