Water → 6-amino-8-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 896189ノート

反応式

HRID 896189 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N+:14]([O-])=O)[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[C:9](=[O:13])[CH2:8][CH2:7]2.O.[Cl-].[NH4+].ClCCl>C(O)C.[Fe]>[NH2:14][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([F:1])[CH:3]=1)[N:10]([CH3:12])[C:9](=[O:13])[CH2:8][CH2:7]2

参加物

7

反応物 4

HCID 962WaterHCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 218779148-fluoro-1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-one

生成物 1

HCID 218777156-amino-8-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one収率 100%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

8-Fluoro-1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-one (Step 2, 2.28 g, 0.0102 mol) is heated in ethanol (75 ml) until dissolved. Water (25 ml) and ammonium chloride (5.46 g, 0.102 mol) are added and the mixture heated to 90° C. Iron powder (2.27 g, 0.0407 mol) is added portionwise and the mixture stirred and heated for 30 minutes. The reaction is cooled and dichloromethane (200 ml) added. The mixture is filtered and the organic layer separated, washed with saline, dried (MgSO4) and evaporated to give the title compound as a yellow solid (1.98 g, 99%); [M+H]+=195.

後処理

  1. dissolutionuntil dissolved
  2. temperatureheated for 30 minutes
  3. temperatureThe reaction is cooled
  4. filtrationThe mixture is filtered
  5. customthe organic layer separated
  6. washwashed with saline
  7. dry with materialdried (MgSO4)
  8. customevaporated

出典と根拠

ORDレコード
ord-aa46db9b8cc14728b1b748490c8da0d1
出典データセット
uspto-grants-2005_07
特許番号
US06919329B2

反応ノート

読み込み中…