Potassium Carbonate → HCID 86675387, compound

HRID 526267Notes

Reaction equation

HRID 526267 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=2[O:18][CH3:19])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH3:26][O:27][C:28](=[O:31])[CH2:29]Br.C(COC1C=CC(N=NC2C=CC(CO)=CC=2)=CC=1)(OC)=O>CC(C)=O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:29][C:28]([O:27][CH3:26])=[O:31])=[CH:13][C:12]=2[O:18][CH3:19])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 866753864-(4-(Carbomethoxy)methoxyphenylazo)benzyl alcoholHCID 1364132044-((4-(Hydroxymethyl)phenyl)diazenyl)-3-methoxyphenol

Product 1

HCID 86675387HCID 86675387, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 2 (0.375 g, 1.45 mmol) was dissolved in 20 mL anhydrous acetone to which K2CO3 (0.6 g, 4.35 mmol) was added, followed by methyl-bromoacetate (0.15 mL, 1.59 mmol) at room temperature and reaction mixture stirred for 12 hours. The remaining procedure was followed as described for compound 3 to obtain compound 4. Yield: 0.41 g (86%). 1H NMR (500 MHz, CD3SOCD3) δ 3.71 (s, 3H, H, (OMe)), 3.94 (s, 3H, aromatic-OCH3), 4.56 (d, 2H, J=6.0 Hz, Hf), 4.93 (s, 2H, Hl), 5.34 (t, 1H, J=6.0 Hz, —OH), 6.54-6.64 (m, 1H, Hb), 6.78-6.82 (m, 1H, Hc), 7.45-7.49 (m, 2H, He), 7.57-7.61 (m, 1H, Ha), 7.73-7.78 (m, 2H, Hd). 13C NMR (125 MHz, CD3SOCD3) δ 51.96 (Cm), 52.2 (aromatic-OMe), 62.5 (Cf), 64.8 (Cl), 100.0 (Cc), 106.4 (Cb), 117.2 (Ci), 122.1 (Cd), 127.0 (Ce), 136.2 (Ca), 145.3 (Ck), 151.4 (Cj), 158.4 (Ch), 161.7 (Cg), 168.8 (CO). ESI-MS: [M+H]+ C17H19N2O5 calcd 331.1294, obsd 331.11.

Workup

  1. additionwas added
  2. customreaction mixture

Sources & evidence

ORD record
ord-329c9afb62fe4055a4581f78fe7d9b7f
Source dataset
uspto-grants-2016_05
Patent number
US09345781B2

Reaction notes

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