Trimethylsilyldiazomethane → Methyl 2-(quinoxalin-6-yl)acetate

HRID 1661832Notes

Reaction equation

HRID 1661832 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.CO>[CH3:1][O:20][C:19](=[O:21])[CH2:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:8]=[CH:9][CH:10]=[N:11]2

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 184369162-(Quinoxalin-6-yl)acetic acid

Product 1

HCID 67428601Methyl 2-(quinoxalin-6-yl)acetate

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

Trimethylsilyldiazomethane [2.0M in hexanes] (0.08 mL) was added dropwise to a solution of quinoxalin-6-yl-acetic acid (0.030 g, 0.159 mmol) in toluene/methanol [8/1] (0.5 mL) and stirred until the bubbling stopped. The reaction was then evaporated and the crude product was purified via silica gel column chromatography in hexane:ethyl acetate (1:1) to give 0.013 g of quinoxalin-6-yl-acetic acid methyl ester. This was added to a solution of hydrazine (0.10 mL) in methanol and stirred at room temperature overnight. The reaction mixture was evaporated in vacuo to give 0.019 g of quinoxalin-6-yl-acetic acid hydrazide. 1H NMR (400 MHz, DMSO-d6) δ 9.77 (bs, 1H), 9.35 (m, 2H), 8.46 (d, 1H, J=8.8 Hz), 8.39 (m, 1H), 8.19 (dd, 1H, J=2.0, 8.8 Hz), 4.68 (bs, 2H), 4.07 (s, 2H).

Workup

  1. customThe reaction was then evaporated
  2. customthe crude product was purified via silica gel column chromatography in hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-b81568e99bf44958a93060995969619e
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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