Methyl Anthranilate → HCID 12515832, compound

Temperature

0 °C

To methyl anthranilate (5 g, 33.1 mmol) stirring in DCM at 0° C. under N2 was added DIEA (5.1 g, 39.7 mmol) in one portion followed by the dropwise addition of 2-chloropropionyl chloride (4.2 g, 33.1 mmol). The reaction was allowed to stir at 0° C. for 30 min. then warmed to room temperature, stirring for an additional 3 h. The reaction was treated with saturated aqueous solution of NaHCO3 and the resulting biphasic mixture transferred to a separatory funnel. The layers separated and the aqueous layer was extracted twice more with DCM (25 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated under vacuum to afford the desired product (7.75 g, 97% yield), which was used without further purification. 1H-NMR (CDCl3): δ 11.8 (br, 1H), 8.72 (dd, 1H), 8.08 (dd, 1H), 7.58 (m, 1H), 7.15 (m, 1H), 4.56 (q, 1H), 3.97 (s, 3H), 1.85 (d, 3H).

1. temperaturethen warmed to room temperature
2. stirringstirring for an additional 3 h
3. customthe resulting biphasic mixture transferred to a separatory funnel
4. customThe layers separated
5. extractionthe aqueous layer was extracted twice more with DCM (25 mL)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated under vacuum

ORD record

ord-f5eb1e1305ce4d4f9361d55430358e4e

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748440B2