6-methoxy-3,4-dihydroisoquinolin-1(2H)-one → 6-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

HRID 1696524Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2.Cl.[NH+]1C=CC=CC=1>O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 6-methoxy-3,4-dihydroisoquinolin-1(2H)-one (6.40 g, 35.6 mmol) and pyridinium hydrochloride (41.1 g, 356 mmol) was heated at 200° C. for 3 h. Water was added (200 mL) and the mixture was extracted with CH2Cl2 (3×200 mL), dried (MgSO4) and concentrated to yield 6-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (1.60 g, 39%, 2 steps) as a yellow solid. 1H NMR (400 Mhz, acetone-d6): δ 8.91 (brs, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.40 (brs, 1H), 6.77 (d, J=8.4 Hz, 1H), 6.70 (s, 1H), 3.47 (dt, J=6.8, and 3.2 Hz, 2H), 2.88 (t, J=6.6 Hz, 2H); MS (ESI) m/z: 164.0 (M+H+).

Workup

extractionthe mixture was extracted with CH2Cl2 (3×200 mL)
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-f1f1b6812d094614870ca10a10e9ab94
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163756B2

Reaction notes

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