Dimethylamine → 3-(dimethylamino)-N-(3-nitrophenyl)propanamide

HRID 716855Notes

Reaction equation

HRID 716855 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)=[O:5].[CH3:16][NH:17][CH3:18]>C1COCC1>[CH3:16][N:17]([CH3:18])[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 34652363-chloro-N-(3-nitrophenyl)propanamide

Product 1

HCID 866899623-(dimethylamino)-N-(3-nitrophenyl)propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-chloro-N-(3-nitrophenyl)propanamide (4.6 g, 20 mmol) in THF (50 mL) was added dropwise N,N-dimethyl amine (2M solution in THF) (1.8 g, 20 mL, 40 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight and then evaporated to dryness under reduced pressure. The residue was triturated with 5% NH3 (aqueous, 50 mL) and the solid product was collected by filtration, washed with water followed by hexane, and dried to give 3-(dimethylamino)-N-(3-nitrophenyl)propanamide, 4.1 g (87%), mp 80-81° C. 1H NMR (DMSO-d6) δ: 2.17 (6H, s, CH3), 2.47-2.50 (2H, t, J=6.4 Hz, CH), 2.56-2.59 (2H, t, J=6.8 Hz, CH), 7.57-7.62 (1H, t, J=8.2 Hz, Ar—H), 7.88-7.91 (2H, dd, J=8.1 and 2.2 Hz, Ar—H), 8.63-8.64 (1H, t, J=2.0 Hz, Ar—H), 10.49 (1H, brs, NH).

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe residue was triturated with 5% NH3 (aqueous, 50 mL)
  3. filtrationthe solid product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-3c9f5ff5b3d3441983c48a197a31561a
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

Loading…