Water → HCID 14053648, compound

HRID 1762276Notes

Reaction equation

HRID 1762276 reaction equation
[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=2[F:20])[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2.O>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:17][C:15]1[CH:14]=[CH:13][C:12]([F:20])=[C:11]([N:3]2[C:2]([Cl:1])=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]3)=[N:4]2)[CH:16]=1

Participants

6

Reactant 2

HCID 962WaterHCID 14053649HCID 14053649, compound

Product 1

HCID 14053648HCID 14053648, compoundYield 83.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of iron powder (28.75 g) in 5 % aqueous acetic acid (57.5 ml) heated at 80° C., a solution of 3-chloro-2-(2-fluoro-5-nitrophenyl)-4,5,6,7-tetrahydro-2H-indazole (30.45 g) in acetic acid (103 ml) and ethyl acetate (103 ml) was added, and the resultant mixture was heated at a temperature of 60° to 80° C. under reflux for 3 hours. After cooling, water and ethyl acetate were added to the reaction mixture. The residue was removed by filtration. The filtrate was extracted with ethyl acetate, and the extract was washed with water and an aqueous sodium bicarbonate solution, dried and concentrated to give 2-(5-amino-2-fluorophenyl)-3-chloro-4,5,6,7-tetrahydro-2H-indazole (22.97 g). m.p., 120.9° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. customThe residue was removed by filtration
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialan aqueous sodium bicarbonate solution, dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39cd35a813f7460883430a8eb9ccac61
Source dataset
uspto-grants-1989_05
Patent number
US04831150

Reaction notes

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