2-(3,4,5-trimethoxyphenyl)acetamide → HCID 44407457, compound

HRID 1677555Notes

Reaction equation

HRID 1677555 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([C:12](=O)[C:13]([O-])=[O:14])C.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:29][C:30]([NH2:32])=[O:31])[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26]>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:12]1[C:13](=[O:14])[NH:32][C:30](=[O:31])[C:29]=1[C:21]1[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:19]([O:18][CH3:17])[CH:20]=1

Participants

3

Reactant 2

HCID 2816762-(3,4,5-trimethoxyphenyl)acetamideHCID 86636864HCID 86636864, compound

Product 1

HCID 44407457HCID 44407457, compoundYield 98.7%

Procedure

The general procedure was followed using indole-2-ethylglyoxylate (1.0 g, 4.61 mmol); 3,4,5-trimethoxyphenylacetamide (0.8 g, 3.0 mmol) and 1.0 M KOBut (10 ml, 10.0 mmol). Purification was achieved by column chromatography (ethyl acetate/hexanes 1/1) to yield the title compound (1.12 g, 65%) as red crystals. mp=252° C. 1H NMR (DMSO-d6), 300 MHz, δ [ppm]=3.68 (s, 6H, OCH3); 3.75 (s, 3H, OCH3); 6.87 (s, 2H); 6.98 (m, 2H); 7.14 (t, 1H); 7.53 (m, 2H); 11.04 (s, 1H, NH); 11.28 (s, 1H, NH). EI-MS (m/z): 378.7 (M+).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-e2abbc08ce4444a8a59e0bb3e98eeea0
Source dataset
uspto-grants-2011_08
Patent number
US08008320B2

Reaction notes

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