Diisopropylethylamine → HCID 59497474, compound

HRID 1747297Notes

Reaction equation

HRID 1747297 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].Cl.[CH2:14]([O:16][C:17](=[O:21])[CH2:18][CH2:19][NH2:20])[CH3:15].CCN(C(C)C)C(C)C>CC(N(C)C)=O.C(OCC)(=O)C>[CH2:14]([O:16][C:17](=[O:21])[CH2:18][CH2:19][NH:20][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:15]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27833993-Fluoro-4-nitrobenzonitrile

Product 1

HCID 59497474HCID 59497474, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-Fluoro-4-nitrobenzonitrile (1.0 g, 6.0 mmol) in DMA (5 mL) were added Beta-Alanine ethyl ester HCl (1.4 g, 9.03 mmol) and DIPEA (1.6 mL, 9.03 mmol). The reaction mixture was stirred at room temperature for 16 h (the reaction was completed; the reaction mixture turned to orange from yellow in color). The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was then dried over Na2SO4 and concentrated to afford 1.53 g (96%) of the desired product as yellow solid.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fc2764a60cc7477097590e3ac1b8a624
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…