Triethylamine → 2-(Propanoylamino)benzaldehyde

HRID 238231Notes

Reaction equation

HRID 238231 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(N(CC)CC)C.[C:17](Cl)(=[O:20])[CH2:18][CH3:19]>ClCCl>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][C:17](=[O:20])[CH2:18][CH3:19])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 682552-Aminobenzaldehyde

Product 1

HCID 220743032-(Propanoylamino)benzaldehydeYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-aminobenzaldehyde (1.21 g, 10 mmol), and triethylamine (1.39 mL, 10 mmol) in dichloromethane (50 mL) was added propionyl chloride (1.04 mL, 12 mol). The reaction was stirred at room temperature for 3 days. The reaction solution was washed with water and then dried over magnesium sulfate and concentrated in vacuo to yield the crude product (1.65 g, 93%). The product was used without further purification. 1H NMR (400 MHz, CDCl3) δ 11.16 (s, 1H), 9.93 (s, 1H), 8.77 (d, J=8.5 Hz, 1H), 7.67 (d, J=7.7 Hz, 1H), 7.62 (t, J=7.1 Hz, 1H), 7.22 (t, J=7.5 Hz, 1H), 2.51 (q, J=7.6 Hz, 2H), 1.29 (t, J=7.6 Hz, 3H); HPLC ret. time 1.34 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 177.2 (M+1)+.

Workup

  1. washThe reaction solution was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04ec9a7e960c46ab90713a617e6b5132
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

Loading…