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

HRID 896189Notes

Reaction equation

HRID 896189 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aa46db9b8cc14728b1b748490c8da0d1
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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