Ammonium Chloride → 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one

HRID 1991304ノート

反応式

HRID 1991304 の反応式
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:15].[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:2]([CH3:1])[C:3](=[O:15])[CH2:4][CH2:5]2

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 218779431-methyl-6-nitro-3,4-dihydroquinolin-2(1H)-one

生成物 1

HCID 218777566-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one収率 97%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a stirred suspension of 1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-one (Step 2, 1.04 g, 5.05 mmol) in EtOH (10 mL) and water (5 mL) is added ammonium chloride (2.70 g, 10.0 equiv.). To this mixture is added iron powder (0.85 g, 3.0 equiv.) in 3 portions. The resulting mixture is heated at reflux for 2 h and then is cooled to room temperature. The resulting mixture is filtered through celite and the filtrate is further diluted with water (100 mL). The filtrate is extracted with ethyl acetate (2×50 mL) and washed with saline (100 mL). The organic layers are combined, dried over MgSO4 and concentrated under reduced pressure to yield the title compound as a yellow solid (0.86 g, 97%), MS (m/z): 177.5 [M+H]+.

後処理

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 2 h
  3. filtrationThe resulting mixture is filtered through celite
  4. additionthe filtrate is further diluted with water (100 mL)
  5. extractionThe filtrate is extracted with ethyl acetate (2×50 mL)
  6. washwashed with saline (100 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-848ab0b7141c4c7cbc5fedb6d1aedd26
出典データセット
uspto-grants-2010_01
特許番号
US07645781B2

反応ノート

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