Hydrochloric Acid → N1-(3-amino-4-chlorophenyl)-N2,N2-dimethylglycinamide

HRID 1014234Notes

Reaction equation

HRID 1014234 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[CH2:10][N:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[N+:15]([O-])=O.O.Cl>C(O)C.CO>[NH2:15][C:3]1[CH:4]=[C:5]([NH:8][C:9](=[O:14])[CH2:10][N:11]([CH3:12])[CH3:13])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22200564HCID 22200564, compound

Product 1

HCID 16784630N1-(3-amino-4-chlorophenyl)-N2,N2-dimethylglycinamideYield 101.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of N1-(4-chloro-3-nitrophenyl)-N2,N2-dimethylglycinamide (1.0 g, 3.89 mmol), SnCL2×2 H2O (5.26 g, 23.3 mmol, Aldrich), and 1M HCl (2 mL, Aldrich) in absolute ethanol (100 mL) was allowed to stir at RT overnight. The reaction was diluted with methanol (100 mL) and quenched with saturated NaHCO3 (200 mL). After stirring 2 hrs at rt, the emulsion was filtered through a celite pad and filtrate evaporated. The residue was then resuspended in dichloromethane (200 mL), washed with water (200 mL), organic layer concentrated by rotary evaporation, and placed under high vacuum to provide N1-(3-amino-4-chlorophenyl)-N2,N2-dimethylglycinamide (0.9 g, 55%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.22 (s, 6 H) 2.99 (s, 2 H) 5.29 (s, 2 H) 6.68-6.74 (m, 1 H) 7.03 (d, J=8.61 Hz, 1 H) 7.22 (d, J=2.38 Hz, 1 H) 9.49 (s, 1 H). ESIMS (M+H)+=228.

Workup

  1. customquenched with saturated NaHCO3 (200 mL)
  2. stirringAfter stirring 2 hrs at rt
  3. filtrationthe emulsion was filtered through a celite pad and filtrate
  4. customevaporated
  5. washwashed with water (200 mL), organic layer
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-c7ecf5e9bd5d4f7ebbb5fee183880656
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…