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

HRID 1014234ノート

反応式

HRID 1014234 の反応式
[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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22200564HCID 22200564、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c7ecf5e9bd5d4f7ebbb5fee183880656
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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