Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | HCID 68640530 | HCID 68640530 | — |
| Catalyst | Adams' catalyst | HCID 345198 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86651540 | HCID 86651540 | — |
Reaction Steps
A suspension of (B2) 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 and the solvent was reduced in vacuo and the residue pardoned 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, DMSO-d6, 300K) δ 10.0 (1H, s), 8.00 (4H, m), 7.75 (1H, d, J=9.0 Hz), 7.49 (1H, d, J=7.0 Hz), 7.38 (1H, dd, J=8.4, 7.0 Hz), 7.23 (1H, d, J=8.3 Hz), 6.61 (1H, d, J=2.0 Hz), 6.48 (1H, dd, J=8.3, 2.0 Hz), 5.40 (2H, s), 4.71 (2H, s), 3.86 (3H, s), 3.73 (3H, s). MS (ES+) C25H21N3O4 requires: 427, found: 428 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08362030B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-49bf5059f33a4175ac77b8577edfc301 |
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| Source note | uspto-grants-2013_01 |
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