HCID 14625291, compound → HCID 14517660, compound

HRID 1031766Notes

Reaction equation

HRID 1031766 reaction equation
[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[C:15]([N+:17]([O-])=O)[C:14]([O:20][CH2:21][C:22](OCCCC)=[O:23])=[CH:13][C:12]=2[F:29])[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[N:3]([C:11]2[C:12]([F:29])=[CH:13][C:14]3[O:20][CH2:21][C:22](=[O:23])[NH:17][C:15]=3[CH:16]=2)[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 1

HCID 14625291HCID 14625291, compound

Product 1

HCID 14517660HCID 14517660, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 3-chloro-2-(2-fluoro-4-butyloxycarbonylmethoxy-5-nitrophenyl)-4,5,6,7-tetrahydro-2H-indazole (10 g) and iron powders (10 g) in acetic acid was refluxed for 5 hours. After completion of the reaction, the reaction mixture was filtered by the use of celite, and the filtrate was combined with water and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by column chromatography using a mixture of hexane and ethyl acetate as an eluent to give 3chloro-2-[7-fluoro-2H-1,4-benzoxazin-3(4H )-on-6yl]-4,5,6,7-tetrahydro-2H-indazole (6.2 g). nD29.0 1.5628.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered by the use of celite
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified by column chromatography
  7. additiona mixture of hexane and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-a4396c0b8fd348d4a36920756e864fa3
Source dataset
uspto-grants-1990_09
Patent number
US04954626

Reaction notes

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