Ethylenediamine → HCID 57625103, compound

HRID 888446Notes

Reaction equation

HRID 888446 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:17])C(OCC)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:18]([NH2:21])[CH2:19][NH2:20]>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11](=[O:17])[NH:20][CH2:19][CH2:18][N:21]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 15716402Ethyl 4-nitrophenylpyruvate

Product 1

HCID 57625103HCID 57625103, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with ethyl 4-nitrophenylpyruvate (223 mg, 1.00 mmol), 3 pieces of molecular sieves (4-8 mesh, 3A) and anhydrous methanol (10 mL). The resulting solution was cooled to 0° C. with an ice bath and 1,2-ethylenediamine (63 mg, 1.05 mmol) was added dropwise. After addition was complete the reaction was stirred at room temperature for 1 h. After this time the resulting suspension was filtered and the filter cake washed with cold methanol (2×5 mL). The filter cake was dried in an oven at 50° C. overnight under vacuum to afford 31 in 89% yield (196 mg) as a white solid: mp 191-192° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.63 (bs, 1H), 8.26 (d, 2H, J=8.0 Hz), 8.09 (d, 2H, J=8.0 Hz), 3.88 (t, 2H, J=6.5 Hz), 3.37 (m, 2H); MS (ESI+) m/z 220 (M+H).

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. additionAfter addition
  4. filtrationAfter this time the resulting suspension was filtered
  5. washthe filter cake washed with cold methanol (2×5 mL)
  6. customThe filter cake was dried in an oven at 50° C. overnight under vacuum

Sources & evidence

ORD record
ord-ffbffc195e4147579897d3162364ef9d
Source dataset
uspto-grants-2012_08
Patent number
US08247550B2

Reaction notes

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