Pyridine → HCID 59442072, compound

HRID 1014231Notes

Reaction equation

HRID 1014231 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C1COCC1.ClCCCl.N1C=CC=CC=1.Cl.[CH3:28][N:29]([CH3:34])[CH2:30][C:31](Cl)=[O:32]>CN(C1C=CN=CC=1)C.ClCCl>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:31](=[O:32])[CH2:30][N:29]([CH3:34])[CH3:28])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 1049PyridineHCID 677684-Fluoro-3-nitroanilineHCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 21493386Dce thf

Product 1

HCID 59442072HCID 59442072, compoundYield 296.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-fluoro-3-nitroaniline (2.48 g, 15.9 mmol) in 1:1 THF/DCE (200 mL) was added pyridine (7.54 g, 95.4 mmol, Aldrich), 2-dimethylaminoacetyl chloride hydrochloride (0.66 g, 4.20 mmol, Lancaster), and catalytic DMAP (˜0.100 g). After heating at 65° C. for 1.5 hrs, the crude reaction mixture was diluted with dichloromethane (300 mL), washed with saturated NaHCO3 (50 mL), evaporated, and purified by column chromatography (dichloromethane to 5% methanol/dichloromethane) to provide N1-(4-fluoro-3-nitrophenyl)-N2,N2-dimethylglycinamide (3.0 g, 78%) as a brown solid. ESIMS (M+H)+=242.

Workup

  1. customthe crude reaction mixture
  2. washwashed with saturated NaHCO3 (50 mL)
  3. customevaporated
  4. custompurified by column chromatography (dichloromethane to 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-d68641a93a6d41dfa81b841bf26884d5
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…