Hydrocarbostyril → HCID 18615010, compound

HRID 1265254Notes

Reaction equation

O=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.Cl[C:13]([CH3:21])([CH2:15][CH2:16][C:17](Cl)([CH3:19])[CH3:18])[CH3:14].[Cl-].[Cl-].[Cl-].[Al+3].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl.C1COCC1>[CH3:14][C:13]1([CH3:21])[C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][C:6]=2[C:17]([CH3:19])([CH3:18])[CH2:16][CH2:15]1)[NH:3][CH2:2][CH2:11][CH2:10]3

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6,6,9,9-tetramethyl-3,4,6,7-hexahydro-1H-benzo[g]quinolin-2-one (1.0 g, 3.9 mmol, prepared by Friedel-Crafts alkylation/annulation of 2-oxo-1,2,3,4-tetrahydroquinoline with 2,5-dichloro-2,5-dimethylhexane in the presence of aluminum trichloride at ambient temperature in dichloromethane) in THF (10 mL) at ambient temperature was added LiAlH4 (11.7 mmol). The reaction mixture was heated to 80° C. and allowed to stir for 30 minutes. The reaction mixture was poured into aqueous saturated sodium potassium tartrate (100 mL), extracted with EtOAc (100 mL), dried (MgSO4), and concentrated to give 6,6,9,9-tetramethyl-1,2,3,4,6,7,8,9-octahydrobenzo[g]quinoline 978 mg (99%): 1H NMR (400 MHz, CDCl3) δ 6.88(s, 1H ArH), 6.41(s, 1H, ArH), 3.26(t, 2H, J=6.2 Hz, ring CH2), 2.71(t, 2H, J=4.0 Hz, ring CH2), 1.92(m, 2H, ring CH2), 1.63(s, 4H, 2CH2), 1.23(s, 12H, 4CH3).

Workup

extractionextracted with EtOAc (100 mL)
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-9c4c80bd3bee427c80997c63dfe2d414
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545049B1

Reaction notes

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