Triethylamine → 2-(Propanoylamino)benzaldehyde

HRID 1804638Notes

Reaction equation

HRID 1804638 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CCN(CC)CC.[C:17](Cl)(=[O:20])[CH2:18][CH3:19]>C(Cl)Cl>[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 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-aminobenzaldehyde (1 g, 8.26 mmol) and Et3N (1.15 ml, 8.26 mmol) in DCM (50 ml) was added propionyl chloride (0.72 ml, 8.26 mmol) and the resulting mixture stirred at RT for 3 days. The mixture washed with water, sat. NaCl, dried over MgSO4, filtered and evaporated to afford the title compound 1.4 g (96%). 1H NMR (CDCl3): 1.30 (t, J 7.6 Hz, 3H), 2.51 (q, J 7.6 Hz, 2H), 7.23 (m, 1H), 7.62 (m, 1H), 7.69 (m, 1H), 8.78 (m, 1H), 9.94 (s, 1H), 11.19 (brs, 1H).

Workup

  1. washThe mixture washed with water, sat. NaCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f59c8f28322e477499249419b1b8661b
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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