HCID 13687205, compound → HCID 13687203, compound

HRID 1731987Notes

Reaction equation

HRID 1731987 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:19]([CH3:20])=[C:18]3[C:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)=[N:12]2)=[C:4]([F:21])[CH:3]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N:11]2[C:19]([CH3:20])=[C:18]3[C:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)=[N:12]2)=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 1

HCID 13687205HCID 13687205, compound

Product 1

HCID 13687203HCID 13687203, compoundYield 99.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of iron powder (3 g) and a 5% aqueous acetic acid solution (10 ml) was heated at 90° to 100° C. while stirring for 10 minutes. To the resulting mixture, there was dropwise added 2-(4-chloro-2-fluoro-5-nitrophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole (2 g) in acetic acid (10 ml) and ethyl acetate (10 ml), followed by stirring at the same temperature for 1 hour. After cooling, the iron powder was eliminated by filtration, and the filtrate was extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution, dried and concentrated. The crystallized residue was collected by filtration and washed with ether to obtain 1.8 g of 2-(4-chloro-2-fluoro-5-aminophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole, m.p., 107°-108° C.

Workup

  1. stirringby stirring at the same temperature for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe iron powder was eliminated by filtration
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated
  8. filtrationThe crystallized residue was collected by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-907f08d51e9a49718494acd2c8001f5f
Source dataset
uspto-grants-1986_11
Patent number
US04624699

Reaction notes

Loading…