Hydrazine → HCID 178526451, compound

HRID 1678261Notes

Reaction equation

HRID 1678261 reaction equation
[S:1]1[C:5]([C:6]2[C:7](Cl)=[C:8]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=2)[C:9](O)=[O:10])=[CH:4][C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2.[NH2:23][NH2:24]>C(O)(C)C>[S:1]1[C:5]([C:6]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[C:8]3[C:7]=2[NH:24][N:23]=[C:9]3[OH:10])=[CH:4][C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59024103HCID 59024103, compound

Product 1

HCID 178526451HCID 178526451, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-Benzo[b]thiophen-2-yl-2-chloro-5-nitro-benzoic acid (0.11 g, 0.33 mmol), hydrazine (0.35 mL) and isopropyl alcohol (3 mL) was heated to about 90° C. for about 1 hour. The mixture was cooled then the solvents were evaporated under reduced pressure. The residue was treated with 6N aqueous hydrochloric acid (5 mL) the mixture was extracted with ethyl acetate (3×30 mL). The organic extracts were combined then concentrated to give 7-Benzo[b]thiophen-2-yl-5-nitro-1H-indazol-3-ol RP-HPLC (Table 1, Method e) Rt 1.41 min; m/z: (M−H)− 310.24.

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvents were evaporated under reduced pressure
  3. additionThe residue was treated with 6N aqueous hydrochloric acid (5 mL) the mixture
  4. extractionwas extracted with ethyl acetate (3×30 mL)
  5. concentrationThe organic extracts were combined then concentrated

Sources & evidence

ORD record
ord-836c51393bba46cb8187bceaa0cfbe1c
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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