Methyl iodide → HCID 57567348, compound

HRID 2404823Notes

Reaction equation

HRID 2404823 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]([C:15]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9].[CH3:26]I>CC#N>[OH:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]([C:15]2[CH:16]=[N:17][C:18]3[C:23]([C:24]=2[O:25][CH3:26])=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:9])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 575673743-Quinolinecarboxamide, N-[4-(1,1-dimethylethyl)-3-hydroxyphenyl]-1,4-dihydro-4-oxo-

Product 1

HCID 57567348HCID 57567348, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(3-Hydroxy-4-tert-butyl-phenyl)-4-methoxy-quinoline-3-carboxamide (415) was synthesized following the general scheme above reacting N-(3-hydroxy-4-tert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (428) with methyl iodide. 1H NMR (400 MHz, DMSO-d6) δ 12.26 (s, 1H), 9.46 (s, 1H), 8.99 (s, 1H), 8.42 (t, J=4.2 Hz, 1H), 7.95-7.88 (m, 2H), 7.61-7.69 (m, 1H), 7.38 (d, J=2.1 Hz, 1H), 7.10 (d, J=8.4 Hz, 1H), 6.96 (dd, J=8.4, 2.1 Hz, 1H), 4.08 (s, 3H), 1.35 (s, 9H); HPLC ret. time 3.46 min, 10-99% CH3CN, 5 min run; ESI-MS 351.5 m/z (MH+).

Sources & evidence

ORD record
ord-0ba972c3709245b985e2affb5a53dda4
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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