HCID 67516649, compound → 7-Chloro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

Temperature

102.5 °C

A mixture of 2-ethyl 3-methyl 7-chloro-3,4-dihydroisoquinoline-2,3(1 H)-dicarboxylate (2.19 g, 7.36 mmol) in 6 M aqueous HCl (30 mL) was heated to 100-105° C. for 2 days. The resulting mixture was concentrated under reduced pressure and triturated with toluene (2×100 mL). Once the supernatant was removed, the solid residue was dried under high vacuum to give 7-chloro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride (1.71 g, 94%) as a faint yellow solid which was used in the next step without further purification. 1H NMR (DMSO-d6, 400 MHz) δ 14.2 (bs, ˜1 H), 10.0 (bs, ˜2 H), 7.41 (s, 1 H), 7.32 (m, 2 H), 4.40 (m, 1 H), 4.32 (m, 2 H), 3.32 (dd, J=17, 4.9 Hz, 1 H), 3.10 (dd, J=17, 11 Hz). LC-MS gives ESI+ MS found for C10H10ClNO2 m/z 212.1 (M+H).

1. concentrationThe resulting mixture was concentrated under reduced pressure
2. customtriturated with toluene (2×100 mL)
3. customOnce the supernatant was removed
4. customthe solid residue was dried under high vacuum

ORD record

ord-c3188acfa6994a808ec4b8cc5645e88f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233985B2