Methyl iodide → HCID 12994069, compound

HRID 1581757Notes

Reaction equation

[H-].[Na+].[CH3:3]I.[OH:5][C:6]([C:11]1[CH:24]=[CH:23][C:22]2[C:13](=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[CH:17][CH:16]=[N:15]3)[N:12]=1)([CH3:10])[CH:7]([CH3:9])[CH3:8]>>[CH3:3][O:5][C:6]([C:11]1[CH:24]=[CH:23][C:22]2[C:13](=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[CH:17][CH:16]=[N:15]3)[N:12]=1)([CH3:10])[CH:7]([CH3:9])[CH3:8]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 10015777HCID 10015777, compound

Product 1

HCID 12994069HCID 12994069, compoundYield 100.3%

Procedure

By employing General Procedure II, NaH (0.020 g, 0.74 mmol), methyl iodide (0.046 mL, 0.74 mmol), and the corresponding 1-hydroxy-1,2-dimethylpropyl phenanthroline (0.052 g, 0.185 mmol), prepared as described by Example 4, were reacted to yield 0.052 g (70% yield) of the title methyl ether as a colorless oil: 1H NMR (300 MHz, CDCl3) δ9.24 (dd, J=4.40, 1.80 Hz, Hp9), 8.24 (dd, J=8.10, 1.80 Hz, Hp7), 8.11 (d, J=8.40 Hz, Hp4), 7.88 (d, J=8.40 Hz, Hp3), 7.81 and 7.74 (two d, J=8.80 Hz, Hp5 and Hp6), 7.60 (dd, J=8.10, 4.50 Hz, Hp8), 3.17 (s, OCH3), 2.25 (sep, J=6.80 Hz, CH(CH3)CH3),1.88 (s, CH3), 1.00 (d, J=6.60 Hz, CH(CH3)CH3), 0.71 (d, J=6.90 Hz, CH(CH3)CH3); 13C NMR (75 MHz) δ165.28, 150.46, 146.51, 145.13, 136.07, 135.76, 128.87, 127/39, 126.46, 126.07, 122.49, 121.06, 84.40, 51.25 39.10, 17.72, 17.43, 16.64; IR (CHCl3 2961 (C—H Ar), 2928 (CH), 866.4 (C—H Ar) cm−1; HRMS m/e Calcd for C18H21N2O (MH+): 281.1654, found 281.1651.

Workup

customwere reacted

Sources & evidence

ORD record: ord-1d560408d3fd4f269582dce1a1b978ea
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06730788B1

Reaction notes

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