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

HRID 1991325노트

반응식

HRID 1991325 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-746d9aebc3ee40c4a2133c3c823e496a
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645781B2

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