2-Naphthol → 1,2,3,4-Tetrahydroisoquinoline

HRID 1928557Notes

Reaction equation

HRID 1928557 reaction equation
C1C2C(=CC=CC=2)C=CC=1O.C1([C@H:18]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[N:19]2)C=CC=CC=1>>[CH2:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27][CH2:18][NH:19]1

Participants

3

Reactant 2

HCID 86632-NaphtholHCID 12143188HCID 12143188, compound

Product 1

HCID 70461,2,3,4-TetrahydroisoquinolineYield 213.3%

Conditions

Temperature
80 °C

Procedure

2-Naphthol (2.09 g, 14.5 mmol) was placed in a flask under nitrogen and (R)-3,4-dihydro-3-phenylisoquinoline 3.0 g (14.5 mmol) was added. The resulting mixture was stirred overnight at 80° C., whereupon no liquid remained. The resulting mixture was recrystallized from Et2O and collected to yield product 4 (4.12 g, 81% yield) as a solid. 1H NMR (CDCl3, 400 MHz, ppm): δ 11.85 (s, 1H), 8.09 (d, J=8.8 Hz, 1H), 7.84 (dd, J=8.4 Hz, J=31.2 Hz, 2H), 7.56-7.12 (m, 10H), 6.97-6.93 (m, 1H), 6.72 (d, J=8.0 Hz, 1H), 6.03 (s, 1H), 4.36 (dd, J=3.6 Hz, J=11.2 Hz, 1H), 3.38 (m, 1H), 3.16 (d, J=14.4 Hz, 1H), 2.80 (s, 1H); 13C NMR (CDCl3, 100 MHz, ppm): δ 155.74, 142.57, 135.61, 133.98, 133.37, 129.88, 128.89, 128.57, 128.37, 128.09, 127.01, 126.88, 126.84, 126.48, 122.67, 121.39, 120.12, 118.11, 59.31, 56.68, 38.38; HRMS calcd. for C25H22NO+1 (M+1): 352.1701. found: 275.1696.

Workup

  1. customThe resulting mixture was recrystallized from Et2O
  2. customcollected

Sources & evidence

ORD record
ord-95d2a7d7d9274d2c9e8fbd8673a3ee67
Source dataset
uspto-grants-2012_05
Patent number
US08183378B2

Reaction notes

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