Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 68574436 | HCID 68574436 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Product | HCID 68577120 | HCID 68577120 | 95% |
Reaction Steps
A mixture of (6-bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (see example 2, step A) (500 mg, 1.46 mmol), zinc cyanide (188 mg, 1.6 mmol) and tetrakis-(triphenylphosphine)-palladium (168 mg, 0.145 mmol) in DMF (5 ml) was heated at 160° C. for 15 min in a microwave reactor. The reaction mixture was poured into water (30 ml) and extracted with diethyl ether (2×50 ml). The combined organic layers were washed with brine (2×30 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel to yield 2-(2-methoxy-benzylamino)-quinoline-6-carbonitrile as light red oil (400 mg, 95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08399674B2 |
|---|
| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-1f1e080374914dbf9a19437e29e661b3 |
|---|
| Source note | uspto-grants-2013_03 |
|---|