Aniline → HCID 59374988、化合物

温度

150 °C

Step 3 Thionyl chloride (0.111 mL, 1.524 mmol) was added to a solution of benzotriazole (594 mg, 4.99 mmol) in DCM (8 mL) at rt and the mixture was stirred for 30 min. A solution of 3-bromo-6-hydroxy-2-methylbenzoic acid (320 mg, 1.385 mmol) in THF (8.00 mL) was added and the mixture was stirred at rt for 2 hrs. The mixture was filtered and the solid was washed with DCM (3 mL). The filtrate was concentrated, and the residue was dissolved in aniline (2 g, 21.48 mmol) and heated in a sealed tube by microwave irradiation at 150° C. for 10 min. The mixture was diluted with EtOAc (100 mL) and washed with 2 M hydrochloric acid (20 mL), water (10 mL) and brine (10 mL), dried and concentrated. The residue was triturated with DCM (4 mL) to give the 3-bromo-6-hydroxy-2-methyl-N-phenylbenzamide as light-colored solid (290 mg, 68%). Mass spectrum m/z 306, 308 (M+H)+.

1. stirringthe mixture was stirred at rt for 2 hrs
2. filtrationThe mixture was filtered
3. washthe solid was washed with DCM (3 mL)
4. concentrationThe filtrate was concentrated
5. washwashed with 2 M hydrochloric acid (20 mL), water (10 mL) and brine (10 mL)
6. customdried
7. concentrationconcentrated
8. customThe residue was triturated with DCM (4 mL)

ORDレコード

ord-f4ced408da1d45c3b3fc541e7389ffb1

出典データセット

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08084620B2