Methylamine → N-methylquinolin-6-amine

HRID 2266970Notes

Reaction equation

HRID 2266970 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH3:12][NH2:13].CC([O-])(C)C.[Na+]>CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+].CC(O)(C)C>[CH3:12][NH:13][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 6329MethylamineHCID 691636-ChloroquinolineHCID 23676156Sodium t-butoxide

Product 1

HCID 12765505N-methylquinolin-6-amineYield 95%

Reagents, catalysts & solvents 2

HCID 25112666BrettPhos PalladacycleCatalystHCID 6386tert-ButanolSolvent

Procedure

Following general procedure A, a mixture of 6-chloroquinoline (164 mg, 1.0 mmol), 2M methylamine (1 mL, 2.0 mmol), NaOt-Bu (120 mg, 1.2 mmol), BrettPhos precatalyst 10 (8 mg, 0.01 mmol), and t-BuOH (1 mL) was stirred at room temperature for 17 h. The crude product was purified via column chromatography (99:1 to 97:3 CH2Cl2/MeOH gradient) to provide the title compound as a yellow oil (150 mg, 95%). 1H NMR (400 MHz, CDCl3) δ: 8.62 (dd, J=4.2, 1.7 Hz, 1H), 7.94 (d, J=8.3 Hz, 1H), 7.88 (d, J=9.1 Hz, 1H), 7.26 (dd, J=8.3, 4.2 Hz, 1H), 7.09 (dd, J=9.1, 2.6 Hz, 1H), 6.68 (d, J=2.6 Hz, 1H), 4.19 (bs, 1H), 2.93 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 147.4, 146.1, 143.3, 133.9, 130.3, 130.2, 121.5, 102.4, 30.8 ppm.

Workup

  1. customThe crude product was purified via column chromatography (99:1 to 97:3 CH2Cl2/MeOH gradient)

Sources & evidence

ORD record
ord-e17e88167447411f9154e2d2ebeb7382
Source dataset
uspto-grants-2010_12
Patent number
US07858784B2

Reaction notes

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