Methylamine → HCID 178441051, compound

HRID 626196Notes

Reaction equation

HRID 626196 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[C:12](\[C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[N:19][CH:20]=2)/[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:29][NH2:30]>CO>[OH:28][C:25]1[CH:26]=[CH:27][C:22](/[C:11](/[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:30][CH3:29])=[CH:6][CH:7]=2)=[C:12](/[C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[N:19][CH:20]=2)\[CH2:13][CH3:14])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 178441050HCID 178441050, compound

Product 1

HCID 178441051HCID 178441051, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the same procedure as described in example 11, step D, (Z)-5-(1-(4-(2-chloroethoxy)phenyl)-1-(4-hydroxyphenyl)but-1-en-2-yl)pyridin-2-ol (0.02 g, 1.0 eq) was reacted with MeNH2 (30% wt in water, 10 mL) in MeOH (20 mL) under reflux to give the desired product. 1H NMR (400 MHz, DMSO-d6) δ 9.37 (brs, 1H), 7.13 (dd, J=9.2 Hz, 2.8 Hz, 1H), 6.96 (s, 1H), 6.91 (d, J=8.8 Hz, 2H), 6.81 (d, J=8.4 Hz, 2H), 6.71 (d, J=8.4 Hz, 4H), 6.12 (d, J=9.2 Hz, 1H), 3.97 (t, J=5.6 Hz, 2H), 2.93 (t, J=5.6 Hz, 2H), 2.40 (s, 3H), 2.29 (q, J=7.2 Hz, 2H), 0.90 (t, J=7.2 Hz, 3H); m/z=391[M+1]+.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-7d9ea6bd3d484070969a504a4a5db1d5
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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