HCID 22163892, compound → HCID 22163889, compound

Temperature

70 °C

To 270 g of polyphosphoric acid heated to 70° C. was added, portionwise, 31.9 g of the product from Step A over 15 min with mechanical stirring under a nitrogen atmosphere. After heating at 70° C. for an additional 45 min, the reaction mixture was cooled to 0° C. and 150 ml of water was carefully added followed by 100 ml of ether. The resulting mixture was further diluted with 170 ml of water and 110 ml of ether. The layers were separated and the aqueous layer was extracted with ether (2×200 ml). The combined ether layers were washed with 100 ml of 1N NaOH and were then dried (MgSO4) and concentrated under reduced pressure to give 25.8 g of a yellow solid. The 1H NMR was consistent with a 68:32 mixture of the structure for Step B and its 5-chloro isomer, respectively.

1. additionwas added
2. temperaturethe reaction mixture was cooled to 0° C.
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with ether (2×200 ml)
5. washThe combined ether layers were washed with 100 ml of 1N NaOH
6. dry with materialwere then dried (MgSO4)
7. concentrationconcentrated under reduced pressure

ORD record

ord-e1340c83ccec4fe8a30b0ba30325b474

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04960784